If you’re here, that means you’re probably planning an epic New England road trip along the coast, and man, I’m SO excited for you! Hi, my name is Sam, and I’ve been exploring this corner of the world for over 15 years now. I’ve taken countless road trips along the coast, and I’ve finally perfected my unforgettable Boston to Bar Harbor, Maine itinerary for those looking to explore the New England coast.
To date, this is my favorite road trip I’ve done, and I can’t wait for you to experience it for yourself. To help you plan the perfect adventure, I’m going to share all my expertise on this area with you, offer my best tips for planning your trip, and give you my ultimate itinerary that was years in the making.
While following along, I encourage you to tailor this itinerary to your own preferences depending on how much time you have for your trip, but I do make suggestions on how long it takes to make the drive, and see all the best places on the way.
Are you ready to start planning together? Let’s go!
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Road Tripping From Boston To Bar Harbor – The Basics
Before we jump into the itinerary, let’s get started with some questions you may have …
How Long Is The Drive From Boston To Bar Harbor?
If you don’t make any stops at all, and take the most direct route, the drive takes between 4 hours and 40 minutes to 5 hours, and spans about 280 miles. It could be longer depending on traffic getting out of Boston. If you happen to leave Boston during rush hour, definitely expect it to take a bit longer.
However, if taking a road trip, you could really make this drive as long as you wanted because there are so many amazing things to see along the way, and some fun detours to take. In just a sec, I’ll give you my suggestions on how long you need to make this trip and see as much of the coast as you can 😉
Is The Drive Scenic?
I think so, yes! But it kind of depends on your expectations.
While many parts of the actual drive are on highways that are kind of boring, there are so many great places to stop along the way that can make the drive very scenic. Especially if you take some of my suggested detours and scenic byways! But is every second of the drive stunning? Well, no. So it’s good to set expectations. It’s really more about the stops you make during the trip than the actual drive itself.
There are some portions of the actual drive that are very beautiful, though.
How Many Days Do You Need To Drive From Boston To Bar Harbor?
Since there are just tons of incredible things to see, I’m recommending one week, or 7-8 days, as I know that this is how much most people have to make this drive. If you have longer than a week, then I say it’s worth it to enjoy going at a slower pace. But you can definitely enjoy the top things to see in a week. This will also include two days in Acadia National Park! For my itinerary, I’m mapping out 8 incredible days for you, and you can adjust it to fit your schedule 😊
Best Time Of Year To Drive Boston To Bar Harbor
Generally, June-September is the best time to drive from Boston to Bar Harbor, as this is when you can expect the best weather, and longest days. July and August is considered peak season along the New England coastline, so this is also when you can anticipate the most crowds and highest hotel prices. But gosh, it’s so worth it!
However, I’ve done this road trip in all seasons – yep, in spring, summer, fall, and even winter! As a second suggestion, I love May to avoid some of the crowds and still enjoy mild weather, and also October to chase all the stunning fall foliage.
I’m going to give you some suggestions later in the post to turn this drive into a fall foliage adventure, so be sure to check that out if you’re planning your trip in the fall season 🍁😉
It’s also good to know that some places along the New England coast are seasonal, especially seafood shacks, boat tours, and ice cream places. If they’re seasonal businesses, it’s likely they won’t open until late May or June and begin to close down around Labor Day or only stay open possibly mid-October. But you’ll always be able to find places that are open year-round, too.
How Many Days Should You Spend In Acadia National Park?
Speaking of Acadia, that’s probably the reason you’re making this drive, right? This park is undoubtedly the top attraction in New England, and rightfully so. I always recommend a minimum of two days to explore, allowing 1 full day in the park, and then at least a half day to see Bar Harbor, which is such a charming town along the coast.
If you have more than a week for this trip, you could definitely add an extra day to Bar Harbor so you have two full days to explore the park.
Is There A Ferry From Boston To Bar Harbor?
No, there is no ferry that goes between Boston and Bar Harbor. The best way to make the trip is to drive.
The only ferry to Bar Harbor is the one from Nova Scotia, which is the CAT Ferry.
Is It Worth Going All The Way To Bar Harbor?
Oh yes! I often get asked this because Bar Harbor is pretty far up the Maine coast, and it’s one of the top attractions most out of the way in New England. But yes, Acadia National Park is absolutely worth the drive. Because there are so many great things to see along the way, and since Acadia offers some of the best and most iconic coastline views in the Northeast, it’s very much worth the effort. It’s always on my list of best places to visit in New England.
Overview: Best Stops To Make When Driving Boston To Bar Harbor
These are the top places I recommend stopping in that I think are very much worth your time. Some of them require a bit of a detour, but depending on your preferences, you’ll probably be happy you went out of your way!
→ Massachusetts North Shore: This includes Marblehead, Salem, Gloucester, Rockport, Ipswich, and Newburyport. I suggest you drive the Essex Scenic Coastal Byway on your way to or from Bar Harbor to see some of these towns, depending on which appeals to you the most. I have a slight preference for Salem, Marblehead, and Rockport, which are all small and easy to do in a couple of hours each. I’ll go more into this later in the post 😉
→ Portsmouth, New Hampshire: Pretty much just off I-95 and not out of the way at all, Portsmouth is a charming coastal city that feels more like a quaint town. Great historic New England scenery and shopping! I recommend this stop if you’re looking for more of a town vibe vs. coastline, as the coastal views here aren’t as impressive as the rest of the places on this list.
→ Southern Maine Coast: This includes places like York & Cape Neddick, Kennebunkport, and Ogunquit. I usually suggest stopping at Nubble Lighthouse in York, spending a couple of hours each in Kennebunkport and Ogunquit, and even staying the night in one of these two towns.
→ Portland, Maine: The state’s largest city is filled with lots of maritime charm, amazing dining, lighthouses, and history. If you like cities, this may be worth staying a night, but you can also see the highlights in a few hours if you’re not a city person.
→ Freeport, Maine: Home to the flagship L.L. Bean store! It’s not worth it for everyone to stop, but gosh, it’s a pretty cool place to see if you’re looking to pick-up some New England clothing and accessories.
→ Maine’s Midcoast: Between Freeport and Belfast, just before getting to Bar Harbor, there are lots of great towns along the coast to explore in this region, including Harpswell, Boothbay Harbor, Wiscasset, Rockland, and Camden. I have so many suggestions for hidden gems and places to visit along this portion of the drive, which I’ll go more into during the itinerary portion of the post!
The PERFECT Boston To Bar Harbor, Maine Road Trip Itinerary
Overview Of This Itinerary:
Since most people reading this will need to start and end their trip in Boston to catch a flight, that’s how I’m formatting the itinerary. You’ll be making most stops on the way to Bar Harbor, but also saving a few for the drive back so you have something to look forward to 😉
Day 1: Explore Boston.
Day 2: Get an early start and drive to either Kennebunkport or Ogunquit. Spend 1 night.
Day 3: Drive to Portland to explore for a few hours, and then make your way to Camden with a few optional detours for lighthouses and great coastal scenery! End in Camden to spend the night.
Day 4: Spend the morning in Camden, and then drive to Bar Harbor. Enjoy downtown Bar Harbor and grab dinner. Spend two nights here.
Day 5: Explore Acadia National Park during the day, and more of Bar Harbor at night.
Day 6: Drive to Boothbay Harbor to spend 1 night. Take a boat tour.
Day 7: Drive to Portsmouth and spend a few hours enjoying the shops, and drive the Essex Scenic Byway along the Massachusetts North Shore to make your way toward Boston. Stay the night in this area.
Day 8: Arrive back in Boston to head home.
Day 1: Explore Boston
Boston is the perfect starting point for most New England itineraries, but it’s also one of the top places to explore in the region, so you should definitely plan at least a full day in the city!
Rooted in history, packed with New England charm, and filled with exciting dining and cool things to do, you can actually cover a lot of ground in just a day in Boston, including the top highlights.
Here are some of the top things I suggest first-timers do:
→ Take a food tour to get a taste of what this region is all about. I have a detailed guide on all the best Boston food tours to help you pick the best one! But seafood and Italian cuisine are especially great here.
→ Visit the most charming neighborhoods, which are Beacon Hill and the North End. The North End is also where you’ll find the best Italian restaurants.
→ Stroll through the Public Gardens and Boston Common. The Boston Public Garden was the very first in the U.S., and it’s so beautiful and photogenic 😍 Boston Common isn’t as scenic as the Public Garden, but in the fall during foliage season, it’s on fire with color. Plus, they’re both really close to one another.
→ If you’re looking to do some shopping, head to Newbury Street and Copley Place.
→ Visit the New England Aquarium.
→ Explore parts (or all!) of the Freedom Trail, which is a walking tour that takes you to historically significant places around Boston. You can also take this awesome Freedom Trail tour.
→ Grab lunch or coffee at the beautiful and Instagram-worthy Tatte Bakery, which has locations around the city (you’ll see why I recommend it when you walk in 😉).
→ End your day with a nice dinner out. I love Neptune Oyster, but they don’t take reservations, and it can be a long wait time. If that’s not worth it for you, I also love the Union Oyster House for a traditional New England dining experience. But there are so many fantastic places in Boston to choose from.
How To Get Around Boston:
Boston is very walkable, and most of the tourist attractions, which are truly the top things to see in the city, are within walking distance to one another (less than a mile) in the downtown area. If you’re exploring for a day, you likely won’t need to use public transit, but may want to get an Uber or Lyft, which are widely available, just to save time (or if you’re tired!).
Where To Stay In Boston:
All of these suggestions are in great locations, and within walking distance to most everything!
→ Boston Harbor Hotel
→ Revere Hotel Boston Common
→ The Godfrey
Day 2: Drive To Southern Maine
First thing’s first, you’ll want to pick-up your rental car in Boston early in the morning. Then, head out to start your drive to southern Maine! During this part of the trip, you’ll pass through Portsmouth, New Hampshire, but don’t worry, we’re going to stop there on the way back 😉 To get to southern Maine, you’ll hop on I-95.
So, Ogunquit or Kennebunkport? Well, you can do both if you want! Ogunquit is about 25 minutes south of Kennebunkport, and the biggest difference, as mentioned, is that Ogunquit is more of a beach town, whereas Kennebunkport is more of a coastal town. That said, Kennebunkport also has beaches, and Ogunquit is also just as charming – I honestly love both.
Since you’ll pass by Ogunquit on your way to Kennebunkport, you can stop by for a few hours and see the beach, and the cute little town, and then end in Kennebunkport. You’ll want to decide which town to spend the night in – both have plenty of hotels and dining options.
On your way to Ogunquit and Kennebunkport, I also recommend you stop in York, which is just south of Ogunquit.
Notable stops to make in York if you have time:
- Nubble Lighthouse on Cape Neddick – the lighthouse itself is not accessible, as it’s on its own little island, but the viewpoint is really great and worth a stop! It only takes a few minutes.
- Stonewall Kitchen Flagship Store & Café – This New England brand started in Maine, and is now sold in specialty stores all over the country, but the flagship store has everything, and is really fun! The café is also very good, and a lot of people come here for lunch.
- Downtown York – Waterfront scenery, and some cute shops.
- The York Cliff Walk – A pedestrian path along the coast with beautiful views.
*If you’re short on time, I would just do Nubble Lighthouse and maybe Stonewall Kitchen, but if you have time, I do recommend the other two stops.
Best Things To See In Ogunquit In A Day:
→ The charming downtown is filled with shops and eateries.
→ Ogunquit Beach, which is one of the best beaches in Maine!
→ Marginal Way, which is a pedestrian walking path along the coastline that connects downtown Ogunquit with the cute Perkins Cove Harbor. This is my personal favorite thing to do in Ogunquit. The trail is easily accessible from downtown, and is just over 1 mile long each way.
→ Perkins Cove – Once you arrive there after walking Marginal Way, there are some really cute shops to explore, and a lovely bridge that makes for fun photos.
Where To Eat In Ogunquit:
- Ogunquit Beach Lobster House
- Footbridge Lobster in Perkins Cove for a lobster roll!
- BeachFire Bar & Grille
Psst! I have an entire guide on things to do in Ogunquit, if you’re looking for more ideas!
Best Things To See In Kennebunkport In A Day:
→ The adorable downtown, which is mainly Dock Square. You’ll find colorful storefronts and great restaurants here.
→ Drive to Cape Porpoise, where you’ll find beautiful coastal New England scenery, and the cute Farm + Table shop.
→ Enjoy the views of the cove from Kennebunkport Bridge (right at Dock Square).
→ Take a coastal walk on Parsons Way.
→ If you have time, head out on a lobster tour with Rugosa.
Where To Eat In Kennebunkport:
- Allison’s Restaurant for a great casual meal
- Cape Porpoise Lobster Co. for a lobster roll!
- Old Vines Wine Bar
Day 3: Drive To Portland & Make Your Way To Camden
This day ends in the beautiful coastal town of Camden, but you’ll be making some fun stops along the way! You can make this day easy by just driving to Portland, and then driving straight to Camden, or you can make it longer and more adventurous by making as many stops you as you feel like. Take a look at all my suggestions, and plan according to your preferences 😊
Option to add a night in Portland: The reason I have you scheduled to only stop in Portland for the day is because it’s such a short drive from Kennebunkport and Ogunquit, and personally, I think the scenery around the Camden area is more quintessential Maine. However, if you have extra time, you can definitely stay the night in Portland, and continue on to Camden the next day!
Things To Do In Portland In A Few Hours:
→ Take a food tour! Portland is a huge foodie destination, and this is a great way to taste your way through the city. The Old Port Seafood Lovers Tour, and Old Port Culinary Walking Tour are both great options.
→ Visit the lighthouses. If you only have time for one, definitely make it Portland Head Lighthouse. This is probably the most iconic lighthouse in New England, and it’s absolutely beautiful. Nearby are also Spring Point Ledge Light, and Bug Light, which are smaller, but still fun to visit. These are all in South Portland, so you’ll want to see them first before getting to downtown Portland.
→ Stroll around Old Port. I suggest parking somewhere around Commercial Street, and then walking around from there. This is the most unique and charming part of the city along the waterfront. Exchange Street and the streets nearby are nice shopping areas, too.
Optional Stops That Are Worth Your Time On The Way To Camden:
Some of these will definitely add time to your trip, so map them out carefully based on your plans to ensure you have enough time in your day.
→ Freeport to shop at the L.L. Bean Flagship Campus.
→ Wiscasset – a charming little town with a famous seafood stand called Reds Eats. Also known as being the prettiest village in Maine. You’ll drive right through it on your way to Camden.
→ Pemaquid Lighthouse – a beautiful lighthouse surrounded by dramatic coastline and parks. There is a small fee to enter the grounds, and it’s cash only.
→ Moody’s Diner in Waldsboro is right on your way on the righthand side, making it a little too easy to swing in for one of their famous whoopie pies! It even made my list of the best whoopie pies in Maine.
→ Marshall Point Lighthouse in Port Clyde. This famous lighthouse was featured in the movie Forrest Gump, and it’s such a beautiful area to visit. This is the lighthouse in my homepage photo!
→ Owls Head is a small town that’s not too far of a detour, and is home to Owls Head Lighthouse, and some beautiful coastal scenery. This is one of my top, most favorite lighthouses in New England.
→ Rockland is a charming little coastal town with a great Main Street for shopping. Also home to Rockland Breakwater Lighthouse.
Notes: You’ll pass by Boothbay Harbor on this portion of the drive, but don’t worry! You’ll be stopping there for a night on the way back 😉 You can also make some of these stops on Day 6 of this itinerary when you drive from Bar Harbor to Boothbay Harbor.
You’ll want to arrive in Camden around dinnertime, so you can get settled into your hotel, and then explore the town a bit before sunset.
Best Things To Do In Camden:
→ Head out on a sunset windjammer tour!
→ Walk around the harbor to enjoy the idyllic waterfront scenery. Also walk over to the Bay Road Overlook (comes up in Google Maps) for the perfect view of the harbor backdropped by the mountains.
→ Grab dinner at a fabulous restaurant. Some of my favorites are Natalie’s, The Waterfront (yep, that’s the name 😊), and Franny’s Bistro.
→ Get some ice cream for dessert at River Ducks or Camden Cone.
→ Drive the auto road in Camden Hills State Park to the top of Mt. Battie and enjoy the bird’s-eye views of the harbor. This road is only open seasonally, but usually only closed in the winter.
→ Shop the lovely boutiques on Main Street and Bay View.
Day 4: Spend The Morning In Camden & Then Drive To Bar Harbor
Refer to the section above for ideas on things to do in Camden the next day. If you weren’t able to take a sailing tour the night before, I do highly suggest booking one for the next day before you leave – this is one of the best places in Maine for a sailing tour!
⛵︎Here is the Camden sailing tour I recommend:
Windjammer Classic Day Sail
Then, make the drive directly to Bar Harbor. On the way, you’ll cross the Penobscot Narrows Bridge, which is one of only four bridge observatories in the entire world! If you have time, it’s worth a stop to enjoy the views from the observatory. Click here for information and fees for exploring the bridge. But it is completely free to drive over if you’re just passing by.
Things To Do Your First Night In Bar Harbor:
→ Walk around the adorable town.
→ Enjoy sunset from Shore Path right in town, with is a coastal walkway.
→ Grab dinner out. I love Geddy’s, Side Street Café, and the Happy Clam Shack for lobster rolls if you’re up for a short drive outside of town.
→ If you have the time, you could also drive up Cadillac Mountain for sunset. While it’s famous for being one of the first sunrises in the U.S., I also love sunset on a clear night and it’s usually less crowded. Note that this requires advanced planning and reservations late May – October.
Day 5: Explore Acadia National Park
Today’s THE day – Acadia National Park! Known as the “Crown Jewel” of New England, the park spans over 70 acres on Mount Desert Island, and offers some of the most iconic and famous scenery in the region.
Best Things To Do In One Day In Acadia:
→ Start with sunrise at the top of Cadillac Mountain. You can also save this for the following morning. Depending on the time of year, you may have to wake up very early for this, so it’s definitely not for everyone. But if it works with your schedule, I do think it’s worth it. It’s one of the most popular activities in the park for a reason!
Note: Reservations are required late May – October to drive the auto road to the Cadillac Mountain summit. They release 30% of the available reservations 90 days in advance, and 70% of them two days in advance. I recommend setting yourself a reminder to check the weather two days in advance, and if it’s forecasted to be a clear day, making the reservation if this interests you. That way, it’s worth it! If it’s forecasted to be cloudy and foggy, the views won’t be a great. Click here for reservation info.
→ Drive Park Loop Road, which is one of the most scenic roads in the park that offers so much for little effort. Along this road, you can make stops at Sand Beach, walk the Ocean Path, visit Thunder Hole, and see the Otter Cliffs. Of all these, I recommend parking at Sand Beach and walking Ocean Path to Otter Cliffs and back. It’s flat and easy, and passes by the best views in the park!
→ Lunch at Jordan Pond House. Famous for their popovers and incredible views overlooking Jordan Pond, this is such a fun thing to do in the park. If the weather is forecasted to be nice, I recommend making reservations for outside if you can. They also have a take out café if you want a quicker experience.
→ Take a hike, of course! Some easier to moderate hikes in the park that I love are Great Head, Bubble Rock, and Gorham. If you’re looking for an adventurous hike that’s more challenging, Beehive is the most popular in the park. Great Head is especially nice because you start the trail at Sand Beach, and it offers spectacular views of the coastline. And then you can just leave you car in the parking lot and walk Ocean Path.
→ Head to Bass Harbor Lighthouse for sunset. It’s about 30 minutes from Bar Harbor, but on a nice night, sunset here is really beautiful. You’ll need to climb out onto the coastal rocks to see the lighthouse, and parking fills up fast. But if you come prepared with sturdy footwear and arrive early enough, it’s wonderful!
→ If you don’t feel like driving to Bass Harbor Light, I would head back to Bar Harbor to relax and enjoy your last night in town with a dinner out.
→ You can also try to make a reservation for sunset on top of Cadillac Mountain in the park if you weren’t able to go for sunrise!
Psst! I have some more detailed posts on Acadia, including my Perfect Acadia National Park Itinerary, Best Places & Towns To Stay When Visiting Acadia National Park, and the Best Time To Visit Acadia National Park.
Day 6: Drive To Boothbay Harbor
You have the option to start your day with a sunrise on Cadillac Mountain if you weren’t able to plan it the day prior! If you do, I suggest having breakfast at Jeannie’s Great Maine Breakfast in Bar Harbor afterward before heading out. They usually open early in-season for everyone getting up to see the sunrise ☀️
The drive to Boothbay Harbor is about 2 hours and 45 minutes without stops, and you also have the option to take the more scenic route and visit some of the suggested stops I detailed in the Day 3 portion of this itinerary. I would go back and reference those if you want to break up the drive.
Why do I recommend the night in Boothbay Harbor? Well, I just love this little coastal town because of its charm, beautiful scenery, slower pace, and all the amazing boat tour options. From Boothbay Harbor, you can take a boat tour out to a puffin colony, head out on a Schooner, or take a lobster trap haul and lighthouse scenic tour. After exploring Acadia the day prior, it’s nice to stop in a town that forces you to slow down a bit, too.
Best Things To Do In Boothbay Harbor:
→ Take a boat tour! In addition to Camden, this is another one of the best places in Maine for some kind of tour out on the water just because of how many different kinds are offered. Plus, the scenery around this area is absolutely beautiful.
These are the top tours I recommend in Boothbay Harbor:
✓ Schooner Day Sail
✓ Schooner Sunset Sail
✓ Lobster Haul, Lighthouses & Seals Tour
→ Cabbage Island Clambakes! This is SUCH a cool, unique, and authentic Maine experience for dinner. You’ll take a boat from downtown, and be brought to the family’s private island for a traditional New England style clam bake dinner, which includes their famous blueberry cake and gorgeous waterfront scenery. Advanced reservations required.
→ Coastal Maine Botanical Gardens. Located just outside of the downtown area, this is such a beautiful place to explore. Don’t forget to snap your photo with the giant wood troll sculptures!
→ Explore the cute and colorful downtown area.
→ Walk the footbridge, which connects both sides of the harbor.
→ Grab ice cream from Downeast Ice Cream, which is one of my favorites in New England.
Where To Eat In Boothbay Harbor:
- Boathouse Bistro
- Boothbay Lobster Wharf
- Shannon’s Unshelled
- Robinson’s Wharf in the neighboring town of Southport is also worth it!
Psst! I have a post all about things to do in Boothbay Harbor, if you want some more ideas 😉
Day 7: Drive To Portsmouth & The Essex Coastal Scenic Byway
Making your way back to Boston, there are so many wonderful places you can stop on the way! In fact, it’ll be hard to choose because there’s a lot you can pack in on this portion of the drive, especially along the Essex Coastal Scenic Byway in Massachusetts.
Customize this day how you’d like, but if you’re feeling ambitious and you have enough daylight hours in your day, you can see Portsmouth, and all the best towns in the along the Scenic Byway.
Things To Do In Portsmouth In A Few Hours:
Portsmouth is very walkable and compact, so you can see the highlights, even with just an hour or two!
→ Market Square, which is the main shopping area downtown. You’ll find lots of great boutiques and eateries in this section of town.
→ Walk down a cute alleyway to Elephantine Bakery for a coffee and a sweet treat.
→ Walk over to Prescott Park for lovely waterfront views and a garden.
→ Visit the Strawbery Banke Museum to see history come to life (open seasonally). If you don’t go to the museum, definitely walk around this area because you’ll see lots of historic houses nearby.
Once you’re done in Portsmouth, take a 30 minute drive to Newburyport and explore there for a bit. This is where I recommend starting the Coastal Byway drive. Follow the Byway through Ipswich, Rockport, Glouster, Manchester By The Sea, and Salem (which is just outside of Boston).
These are the best stops to make along the Essex Coastal Scenic Byway:
→ Newburyport: One of my favorite places to visit in New England, it’s home to amazing shops and such a charming downtown area that sits on the waterfront. Allow about an hour to walk around, grab lattes and whoopie pies from Chococoa Café, and explore the shops.
Psst! I have an entire guide on things to do in Newburyport, MA & Plum Island if you need more info!
→ Crane Estate & Crane Beach in Ipswich. This historic estate is so stunningly beautiful, and the beach nearby is the best on the North Shore. Each requires separate admission fees, and you’ll want to budget your time wisely.
→ Rockport: One of my all-time favorite coastal towns in New England, Rockport is probably the one place I recommend you don’t miss on the drive. It’s very small, but offers an authentic New England fishing village atmosphere with colorful storefronts, lovely art galleries, great dining, and the most painted building in the country – Motif 1 (which was also featured in the movie The Proposal).
Psst! I have an entire guide on things to do in Rockport, MA if you need more ideas!
→ Gloucester is the best place to stop if you have your heart set on a whale watch tour (but you can also take one that departs from Newburyport if that’s more convenient). Whale watch tours in this region are world-class, and head out to the famous Stellwagen Bank National Marine Sanctuary, which is known for its active marine wildlife.
🐋 Click here to check rates & availability for a whale watch tour from Gloucester
Note: While I do love to visit Gloucester, I think with this amount of time, it’s best to focus your itinerary on the other towns along the drive that I’ve recommended, as I think their scenery is more idyllic than Gloucester. Gloucester is also a city, and is bigger and more spread out, so harder to see on limited time. I do recommend it for a whale watch tour, though! If you take the whale watch tour, just know that it will take at least 3 hours, and likely a bit longer.
→ Manchester-By-The-Sea is a beautiful coastal town that can easily be seen in about an hour or so. very picturesque scenery, and it’s home to a lovely beach called Singing Sands.
→ Salem. I’m sure you know it as a top Halloween destination, but it’s honestly great year-round. Filled with historic New England charm, waterfront areas, and some fun places to eat, it’s also very walkable!
Psst! I have an entire guide on taking a Salem, MA day trip and the Best Time To Visit Salem, MA if you want more information for your visit!
→ Marblehead is such a beautiful town along the North Shore just south of Salem that often gets overlooked, but I absolutely love it here. Also filled with historic charm and lovely waterfront scenery, it’s got a quaint Main Street with some cute shops, a beautiful waterfront park, and some nice places to eat.
Psst! I have an entire guide on things to do in Marblehead, MA if you’re looking for more ideas 😉
More Optional Stops: If you’re looking to explore more of Maine’s coast, there are a few more stops you can make on your way from Boothbay Harbor to Boston. I know, I know – I’m probably tempting you to expand your trip even further, but I’m okay with that 😂
→ Georgetown Island to visit Five Island Lobster Company, which is one of the best lobster rolls in Maine you can get. They’re only open seasonally, and the scenery around there it is very quintessential Maine.
→ The Arrowsic Lighthouses. There are two in this area that I really love: Doubling Point and Squirrel Point. Doubling Point requires a drive down a very bumpy dirt road, and Squirrel Point requires about a 3/4 mile hike through the woods, but they’re both beautiful, small lighthouses on the Kennebec River.
Note: Doubling Point is closed until further notice for repairs. I’m monitoring this and will update once renovations are complete!
→ Bailey Island, which is a very small little island that’s accessible by car, and about a 20-minute detour each way. The best thing to see here is the Giant’s Stairs Trail, which offers beautiful coastal views, and giant rocks you can climb around (just practice caution, of course!). There’s also a cute little place to eat right by the bridge called Sundrenched, which is waterfront and has outdoor seating. This is a nice place to get off-the-beaten-path.
Day 8: Head Back To Boston
It’s the end of your trip! Depending on when you need to make your way back home, or to the airport, you may have some time in the morning to explore a few of the places I mentioned above, but I left this day open in case you have to catch an early flight, or start your drive back home early.
If you do happen to have some time on this day to explore, I would suggest you end the previous day in Rockport, and then explore Salem and Marblehead on this day before heading back to the airport.
Optional Itinerary Adjustments
→ If you have more time and are a city person, I would recommend adding a night to Portland and Boston.
→ If you have extra time and don’t want to add a night to a city, I have two suggestions. First option: add a night to Camden to spend a day exploring the nearby attractions (lighthouses, Rockland, etc.) to make the drive from Portland to Camden easier. Second option: add a night to Bar Harbor to see more of the park, and enjoy more hiking.
→ If you have even longer, you could make this a 2-week adventure by driving up the coast of Maine to Lubec, and then crossing the Canada border to the charming town of St. Andrews by the Sea, and Campobello Island. You could also take the CAT ferry from Bar Harbor to Nova Scotia.
I have a detailed guide on visiting Lubec, Maine, if you wanted to explore places further north!
Best Towns To Stay In On The Drive
For an overnight stay, these are my suggestions on the best places to stay based on experience when it comes to options for dining and accommodations (plus, lovely scenery, of course!). You’ll just want to pick where you stay based on how far you want to drive each day.
As you saw in my itinerary, I included some suggestions for overnight stops, but you may want to customize this trip to your liking (which I encourage!), so I wanted to provide you with more options. It’s also good to know that you won’t have time to stay overnight in all these places unless you extend your trip, but you will be able to, at the very least, drive through them all.
→ Rockport, MA: Not far from Boston, and if you’re looking get a leisurely start or slow-burn end to your trip, I really love to recommend a stay in Rockport. Most everything is pretty walkable, with cool shopping, nice hotel options, and idyllic scenery.
Where To Stay In Rockport:
✓ The Cove at Rockport
✓ Addison Choate Boutique Hotel
→ Portsmouth, NH: As mentioned, fantastic dining and shopping, with lots to keep you busy in the evening after you arrive! Plus, the historic charm is really quite lovely.
Where To Stay In Portsmouth:
✓ The Hotel Portsmouth
✓ Hotel Thaxter
→ Kennebunkport OR Ogunquit: Both of these charming coastal towns that are very close to on another, and both make for a great overnight stay. Kennebunkport has more options for nicer accommodations, but Ogunquit has a gorgeous beach. Both have very charming downtowns that are easily walkable with lots of places to eat and shop! Just pick based on what vibe you’re going for: beachy or just traditional coastal.
Where To Stay In Kennebunkport:
✓ Captains Collection Historic Inns
✓ The Boathouse
Where To Stay In Ogunquit:
✓ Anchorage By The Sea
✓ Cliff House: Technically in York, but a short 10-minute drive to Ogunquit. I like to suggest it because it’s a fantastic resort with amazing coastal views, and worth the splurge! It also makes my list of the top New England resorts and spas 😉
→ Boothbay Harbor: I love stopping here for a night or two every time I make this drive. It’s very small and easily seen in a few hours, and I like to stay the night so I have the option to take a boat tour. I also find the shops and restaurants really great.
Where To Stay In Boothbay Harbor:
✓ Harborage Inn On The Waterfront
✓ Spruce Point Inn
→ Camden: Lastly, I think Camden is the best place to stay before reaching Bar Harbor. Built around a gorgeous harbor, the coastal scenery here is beautiful, and it’s a known sailing destination. There’s also a great Main Street for shopping and dining.
Where To Stay In Camden:
✓ Camden Harbour Inn
✓ Lord Camden Inn
Where To See Fall Foliage Between Boston & Bar Harbor
If you happen to be planning your trip to coincide with fall foliage, then I would love for you to consider adjusting the itinerary slightly (but don’t worry, it’s not too different!). Most places already on the itinerary offer amazing foliage color. Here are some suggestions to keep in mind:
→ The Essex Coastal Byway in Massachusetts is GORGEOUS in the fall with lots of foliage color. I’ve done this drive during peak foliage, and I was shocked at how beautiful it was. Manchester-By-The-Sea, Essex, Salem, and Newburyport are especially beautiful in the fall. And, of course, Salem is famous for its October festivities!
→ Portsmouth offers some really lovely fall foliage during this time of the year. It’s also an especially cozy place to visit because of all the historic New England architecture.
→ Boothbay Harbor is also amazing in the fall, and the entire harbor is surrounded in fall color. Head out on a boat tour to see even more beautiful fall foliage! Tours usually end around mid-October, so there are typically opportunities that coincide with peak foliage.
→ Camden is also spectacular in the fall. I definitely recommend hiking or driving up the Mt. Battie Auto Road to take in the views of the harbor from above. It’s the best during foliage season!
→ Kennebunkport also offers some beautiful fall foliage. Having been in October a few times, the fall season always impresses me in this coastal town.
→ Of course, the starting and end points on this road trip are stand-outs in the fall, too. Acadia National Park is stunning in the fall season with foliage color, and Boston is also amazing this time of the year. Although, it’s good to know that Boston tends to peak later in October, so in the fall, you may want to plan to spend more time in Boston at the end of your trip to get a glimpse of some foliage color.
What To Pack For This Road Trip
This will depend entirely on what time of year you visit, so plan accordingly based on the season when it comes to clothing and footwear. Beyond that, here are some things I recommend you bring regardless of what time of year you visit.
→ Light sweater or jacket – even in the summer! If you plan to take any boat tours or get up for sunrise at Cadillac Mountain, you’ll want this to stay warm.
→ Reusable water bottle to stay hydrated.
→ Dramamine if you plan to hop on a boat tour and tend to get seasick.
→ Comfortable shoes – I know this seems obvious, but you can leave your fancy shoes at home. I usually wear a really comfortable pair of sandals in the summer, or sneakers in the spring/fall. If you take a boat tour, they may have some requirements on the type of footwear you wear, so double check that, too.
→ Hiking boots if you plan to tackle any trails in Acadia. You’ll be happy to have the ankle support.
→ Camera, of course! You’re going to see so much incredible scenery on this trip, you’ll want to capture the best memories along the way. This is a good trip to get a tripod if you don’t have one – they even make inexpensive ones for iPhones that are perfect for just about anyone.
Tips For This Road Trip
→ Offline maps on your GPS! You’ll have cell phone service in most places, but when you’re near a beach or inside Acadia National Park, you may lose service.
→ Be ready to pay tolls on the roads. Many highways in New England require tolls to be paid, but most have transitioned to an electronic tolling system. This means you’ll likely cruise right through, and your license plate will be billed if you’re not local, and don’t have EZ Pass. If you’re renting a car, you can ask your rental company how they handle this, but they will more than likely charge your card on file after you return it for the tolls you incurred on the trip. This is pretty standard, and makes everything very easy.
→ Bring Some Cash – I know this seems obvious, but as someone who never carries around cash, I’m always reminded when I make this road trip that some places still don’t take credit cards! Usually places like ice cream stands and seafood shacks are the ones that may be cash only, so it’s good to have a small amount on you at all times. Better yet, get a debit card that reimburses you for ATM fees, like the Charles Schwab checking card. Most places will take cards, though.
→ Prepare for crowds at popular places. Depending on the time of year you take this trip, most places will bring in some level of crowds. The most popular destination is Bar Harbor and Acadia National Park, and this is where you can expect the biggest crowds. If you travel in spring or fall, you’ll see fewer people, but places will still be lively.
→ Prepare for the cost. New England in general is just an expensive region to visit, unfortunately, and prices tend to be higher than other parts of the country.
→ Always be respectful of private property, and never trespass to get the perfect photo. The same goes for not putting yourself or others in danger to get a photo. For example, if you see a beautiful photo spot along a main road, and there’s no place to safely pull over, don’t risk it. There are so many beautiful nooks and crannies around New England that I guarantee you’ll stumble upon a picturesque spot that’s safe to photograph rather often 😉
Looking to expand this road trip into Canada? I’ve got you covered –
✓ My Guide On Traveling Between Bar Harbor, Maine & Nova Scotia
✓ My Maine To Canada Itinerary: A DREAMY East Coast Road Trip
More posts you may enjoy:
- The BEST 7 Day New England Road Trip Itinerary
- The PERFECT Fall Foliage New England Road Trip Itinerary
- The Best Time To Visit New England
- Incredible Lighthouses In New England To See
- Maine Lighthouse Road Trip Itinerary
- Gorgeous New England Islands Worth Visiting
- Maine In The Summer
- Best Places For A Maine Vacation Or Getaway
- Wonderfully Romantic Getaways From Boston
That’s A Wrap On My Boston To Bar Harbor, Maine Road Trip!
And there you have it! After years of perfecting it, I’m thrilled to finally share my unforgettable Boston to Bar Harbor, Maine road trip itinerary with you. I truly believe that the New England coast is such a special and memorable region to experience for yourself, and with this guide, you’ll see the very best it has to offer. Happy planning!
