Driving From Boson to Portland, Maine is one of the best road trips to take in New England because there’s so much you can see in a very short amount of time. If you’re coming from outside of New England, you’ll definitely want to spend a day or two in Boston before taking this road trip, but if you already live in Boston, the payoff along this is really rewarding.
This post is all about the best places to stop on when driving Boston to Portland, Maine, and in each destination, I’ll share all the best sites to see, restaurant recommendations, and the best places to stay overnight. I even have an itinerary for a day trip from Boston to Portland for those who are really short on time! With that, let’s get into it.
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How Long Is The Drive From Boston To Portland, Maine?
This drive can take anywhere from 1 hour and 45 minutes to 2 hours and 15 minutes without any stops, and it all depends on traffic. There’s usually traffic getting in and out of Boston on weekdays, but on weekends, it shouldn’t be quite as bad. I suggest using Google Maps to type in the exact day and time you plan to leave to get a better idea, especially if you’re short on time (taking a day trip, for example).
While most of these suggestions are directly on the way while driving from Boston to Portland, Maine, it will add some extra time, so you’ll want to factor that into your driving time. Once you decide on which stops you want to make (hopefully all of them!), you can then get a better idea of how long your drive will be in total.
Is The Drive From Boston To Portland, Maine Scenic?
It’s very scenic! On this drive, you’ll pass through charming small towns in Massachusetts, visit the best coastal town in New Hampshire, and then begin your drive up the coast of Maine, stopping in some amazing seaside destinations with lots of character and fun things to do.
How Many Days Do You Need When Driving From Boston To Portland, ME?
Anywhere from a day to a week, and it really just depends on how much time you have to dedicate to the trip. This is a really great weekend or long weekend road trip to take, as you’ll have time to stop at most of the destinations on the way there or back. But, I personally suggest about 4-5 days if you have an interest in seeing as much as possible on the drive, and also want a day or two to explore Portland.
For ideas on a day trip from Boston to Portland, keep reading later in the post to see my suggested itinerary!
Overview Of The Drive From Boston To Portland, Maine
There are 10 towns I suggest you stop in while driving Boston to Portland, Maine. They’re all very easy to spend a few hours in before moving on, and depending on how much time you have, you can either do half of them on your way to Portland, and the other half on your way back, or eliminate any that you’ve done before, or don’t have any interest in. Each of these towns is also pretty much on the direct route from Boston to Portland, with minimal diverging off course.
I’ll do a more detailed breakdown of each destination and the best things to do later on, but for now, here’s a breakdown of all the stops you’ll making, including how far they are from one another:
- Salem, MA (30-45 minutes from Boston, depending on traffic)
- Rockport, MA (optional stop because it’s a bit out of the way, 30-40 minutes from Salem)
- Newburyport, MA (40 minutes from Salem, or 45 minutes from Rockport)
- Portsmouth, NH (30 minutes from Newburyport)
- Kittery, ME (10-15 minutes from Portsmouth)
- York, ME (15 minutes from Kittery)
- Ogunquit, ME (15 mins from York)
- Kennebunkport, ME (30 minutes from Ogunquit)
- Old Orchard Beach, ME (30 minutes from Kennebunkport)
- Cape Elizabeth/Portland Head Lighthouse (30-40 minutes from Old Orchard Beach)
- Portland City Center/Old Port (15-20 minutes from Cape Elizabeth/lighthouses)
Best Things To See When Driving From Boston To Portland, Maine
Okay, so now that you know the general route, here’s a detailed breakdown of all the towns you’ll pass through, why they’re worth stopping in, and the best things to do in each one.
1. Salem, MA
Salem is known for its history with the Salem Witch Trials, an of course, all things Halloween, but it’s honestly a really great little place to explore year-round. There’s a lot more to discover besides all the witch history (although, that’s also very fun and interesting).
If passing through while driving Boston to Portland, Maine, I suggest seeing these things in Salem:
- Visit the Salem Witch Memorial.
- Lunch at the Lobster Shanty (go for the lobster martini!).
- Get a grounds ticket to explore The House of Seven Gables (meander through the nearby side streets in the neighborhood for cool historic homes, too).
- Walk by the Witch House (especially if you visit in the fall).
2. Optional Stop: Rockport, MA
I labeled Rockport as optional because to get there, you’ll have to veer a bit off-course from your drive to Portland. But, I think it’s worth it if you have the time, and have never been before. This detour will add just over an hour of driving time (plus any time you spend in Rockport).
Rockport is one of the most unique towns in New England, and because it sits right along the water, it’s incredibly scenic. If you’re a fan of the movie The Proposal, you may also recognize some of the filming locations in Rockport! A few other movies have been filmed here, too.
If passing through while driving Boston to Portland, Maine, I suggest seeing these things in Rockport:
- Explore the unique shops and art galleries along Bearskin Neck
- Head over to Motif 1, the most painted building in the country (just off Bearskin Neck).
- Grab an ice cream from The Ice Cream Store, the cutest little New England ice cream shack.
- Walk down to the end of Bearskin Neck to cross the breakwater jetty.
- If you’re in need of lunch during your visit, Roy Moore Lobster Co. has an awesome lobster roll.
Bonus Suggestion: Drive The Whole Massachusetts North Shore
If you have extra time, you could take your time getting out of Massachusetts, and spend the day driving along the entire North Shore region. I highly suggest this because this is a really beautiful area of New England, and you’ll see some amazing coastal towns, but I would only do this if you’re able to spend at least 3 days for the entire road trip, as this will take up an entire day.
Two of the main towns along the North Shore, Salem and Rockport, are suggested above. But if you’re able to add on this part of the drive, you’ll want to explore these towns in this order, starting in Boston:
- Manchester By The Sea
I have some posts all about this region of Massachusetts to help you get some ideas on what to do in these towns:
3. Newburyport, MA
Newburyport is a really beautiful and picturesque town along the northern coast of Massachusetts that I feel is very underrated. If you make this stop while driving Boston to Portland, Maine, you don’t need to spend a lot of time here, but getting out in Newburyport to stretch your legs, explore the charming Market Square and waterfront park is absolutely worth it.
Here’s what I suggest seeing when stopping in Newburyport for a few hours:
- Explore the charming brick-lined streets of downtown, and visit the cute shops.
- Walk along the waterfront path to admire the views.
- If you’d rather visit something more outdoorsy, head to Plum Island and walk on the shoreline of Plum Island Beach.
- On Plum Island, you can also visit the Parker River National Wildlife Refuge, and I recommend the Hellcat Boardwalk Trail (which is very easy, scenic and relaxing, and not as scary as it sounds).
- Pop into Plum Island Soap Co.
4. Portsmouth, NH
Portsmouth is one of my favorite towns in New Hampshire, and one of the best coastal destinations in the state. This is another great little area that you can easily see in just a few hours, and is also the perfect place to grab a bite to eat, or pick up a snack for your drive from Boston to Portland.
In Portsmouth, you’ll find lots of charming streets, a great little downtown with truly awesome shops, a wonderful bakery (which I’ll list below), and really incredible restaurants.
Here’s what I suggest seeing when stopping in Portsmouth when driving Boston to Portland, Maine:
- Get some treats from Elephantine Bakery (they also do online ordering if you’re short on time!). I especially love their croissants and s’mores brownies.
- Walk through downtown to visit the shops (Sault New England and Jane Gee are two really nice ones).
- Swing by Portsmouth Brewery for a glass of beer.
5. Kittery, ME
Kittery is a fun, quick stop to make, but it’s also one of the ones I would suggest you skip if you’re short on time. Kittery has a couple of scenic areas that make for a nice moment to get our of the car, stretch your legs and snap a photo, but I think most of the other stops mentioned on this list are more worth your time.
I’m definitely not saying that Kittery isn’t worth a stop because it definitely is (or it wouldn’t be on this list!), but if you’re looking to cut out a few stops, I think places like Ogunquit, Portsmouth, Rockport, etc. will provide more fun in exchange for your time. Hopefully that makes sense!
That said, there are some really cool things to visit in Kittery, and here’s my list of places to check out:
- See the Badger Island buoy shack.
- Grab a lobster roll at Bob’s Clam Hut.
- Visit the famous When Pigs Fly Company Store.
- Do a little shopping at the outlets.
6. York, ME & Cape Neddick
York and Cape Neddick are great areas to stop in when driving Boston to Portland, Maine, and offer a nice mix between walking around town to do some shopping and dining, or getting out into nature. In this area, you’ll have options from hiking mountains, visiting beaches, exploring the shops, grabbing a bite to eat and seeing one of the best lighthouses in Maine.
Here’s my list of things to check out in York and Cape Neddick during your drive:
- Visit the Stonewall Kitchen flagship store.
- Hike the Mount Agamenticus trail for spectacular mountain views (especially amazing in the fall!).
- Walk along one of the beaches in York (Long Sands Beach is my personal favorite).
- Take in the views at the Bald Head Cliff.
- Visit Cape Neddick to see Nubble Lighthouse.
7. Ogunquit, ME
Ogunquit is such a fun little coastal town in southern Maine, and it’s one of the destinations I recommend the most if you’re looking for a great mix of beach time and small town charm. I also think it’s one of the best beach towns in New England. It has such a fun downtown area with great shops and restaurants, and the beach in Ogunquit is really stunning.
This is an awesome destination to stop in when driving Boston to Portland, Maine, especially if you’re hoping to hear the sound of the craving waves.
Here’s what I suggest you do in Ogunquit when stopping during your road trip:
- Walk Marginal Way from town in Ogunquit, which ends in Perkins Cove, a small little village in Ogunquit. This pedestrian path along the coastline just over a mile each way, so plan your time accordingly. If you do one thing during your time in Ogunquit, I would say this is it.
- Explore the shops in town (Goods Ogunquit is especially fun to visit).
- Walk along the shores of Ogunquit Beach, which has 3 miles of pristine sand.
- Grab a lobster roll at the Lobster House (right by the beach), and hopefully you can get a table outside.
8. Kennebunkport, ME
I can never decide if I prefer Ogunquit or Kennebunkport, but what I can tell you is, they’re both definitely worth visiting when driving Boston to Portland, Maine. Kennebunkport is a charming little coastal town in southern Maine that has some great shops, amazing restaurants, awesome things to see and some nice beaches to explore. It definitely has its own vibe that is really fun to experience.
Here’s what I suggest you do in Kennebunkport when stopping during your road trip:
- Walk around Dock Square to visit the shops.
- Grab some seafood at the Clam Shack or a lobster roll and chowder at Allison’s.
- Get a drink at Batson River Brewing & Distillery (this is one of my favorite places in New England for a cocktail!).
- Take a drive to Cape Porpoise for nice views of the water (visit the Farm + Table store while there for unique and fun home decor, candles, etc).
- Visit one of the beaches (Gooch’s and Mother’s beaches are my favorites in Kennebunkport).
9. Old Orchard Beach, ME
One of the most iconic sites in southern Maine is the pier at Old Orchard Beach, and this is a cool place to stop when driving from Boston to Portland, Maine because you’ll kind of feel like you’ve stepped back in time.
When I visited, I almost felt as if I was transported to an old-timey state fair, in a good way, of course. You’ll find an old-fashioned pier with vendors selling fried dough, drinks and other street foods. Close to the beach, you’ll find a small amusement park and mini golf places, too.
Here’s what I suggest you do in Old Orchard when stopping during your road trip:
- The best thing to see is Old Orchard Pier right at the beach. Definitely walk around the actual pier, and plan to get a few fun fair foods, for sure! Also, walk along the beach to see it from a distance, and walk under it for some cool photo opportunities.
- If you’re feeling like taking some amusement park few rides, head over to Palace Playland.
- Feel like a kid again at Pirate’s Cove Adventure Mini Golf.
Tip: Expect to pay for parking while visiting Old Orchard, and the closer to the beach you are, the more it will be. On average, parking costs about $20 for the day (many lots didn’t offer by-the-hour parking when I visited). So, if you only want to see the pier and don’t want to pay to park for the whole day, this may be a good stop to skip.
10. Cape Elizabeth, ME
Cape Elizabeth is a town that’s actually part of Portland, but it’s south of the main city, and you’ll get to this part before driving into downtown Portland.
This is where the 3 Portland lighthouses are, and I highly suggest planning time to see all of them. They’re actually very close to one another, which makes it easy to see them all within a couple of hours at most. You can either visit them all before getting into Portland, or depending on your schedule, plan to take a quick drive out to see them during your stay in Portland (if you’re staying overnight).
Since you’re driving from the south, I suggest making these stops in this order in Cape Elizabeth:
- Portland Head Light. This is one of the most iconic sites in Maine, and also the most popular New England lighthouse. You’ll find amazing views here, and if you can only see one lighthouse, this is the one to see.
- If arriving in the morning, I highly recommend stopping at Scratch Bakery before visiting the other two lighthouses. They have awesome bagels, and really delicious baked goods. They also do online ordering, so you can order ahead and pick-up when you arrive to save time.
- If you have time, head over to Willard Beach next. This is a small beach, but what makes it worth the stop is the cute little beach shacks all the way to your right. Walk across the beach to get to them, enjoy the views from there, and then have fun walking along the waterfront path nearby.
- Spring Point Ledge Lighthouse is next, and this is a fun one because you can walk across the entire breakwater and get right up to the cute little lighthouse.
- Bug Light is last, and is located in a small, but really nice, little park. This is one of the most unique lighthouses in New England, as it’s very ornate in its design. It also makes for fun photos.
- After these stops, you can drive off to downtown Portland!
Things To Do Once You Arrive In Portland, Maine
Portland is a cool city to explore, and is packed with history, charming streets and tons and tons of amazing restaurants (this is actually one of the best cities in the Northeast for foodies!). Here are some highlights to check out once you arrive in Portland:
- Old Port district.
- Tour the breweries.
- Walk along the Eastern Promenade.
- Take the ferry to Peaks Island.
- Explore the Portland Observatory.
- Obviously, eat all the delicious food. Click here for an awesome food tour of Portland!
Best Places To Stay During The Drive
If you have time to break up your drive and really enjoy all these fun places to visit, these are the towns I would recommend you stay the night in based on options for things to do, and great restaurants:
Rockport is a really awesome place to spend the night because it has a really cool little shopping district, wonderful restaurants and is overall, a really unique destination. My favorite place to stay is the Addison Choate hotel, which is only a 10-minute walk to Bearskin Neck, and offers really beautiful rooms to stay in.
If you’re looking for a luxury stay while driving Boston to Portland, Maine, Cliff House in Cape Neddick is the perfect place for you. It’s just about half-way between Boston and Portland, and has all the amazing, luxury amenities you’d expect like gorgeously appointed rooms with ocean views, incredible on-site restaurants, a spa and every square inch of their property offering dramatic coastline views.
Ogunquit is one of my favorite coastal towns in Maine, and makes for a great stop to stay the night or two. There are lots of shops and restaurants to choose from, as well as Ogunquit Beach to enjoy. If you’re looking for a nice place to stay by the beach, I really love Terrace By The Sea, which provides ocean views from their front porch (where you can sit and enjoy a glass of wine at sunset!), and is a very short walk to town, or to the ocean.
Kennebunkport is another of my favorite towns for an overnight stay, and one of the best places to book a room is the Cottages at Cabot Cove. This hotel is a grouping of individual cottages that are uniquely decorated, and you’ll get to pick which one you want to stay in when you make your reservation. Each morning, a cooler with breakfast goodies is hung on your door, and you also can use the hotel’s canoes to explore the cove. I have a hard time not staying here when I visit Kennebunkport.
What Is Halfway Between Boston and Portland, Maine?
As mentioned above, York and Cape Neddick are about halfway between Boston and Portland, Maine. Portsmouth, NH and Kittery are also about halfway between the two cities.
Can You Take A Day Trip To Portland, Maine From Boston?
You sure can! The drive will likely average about 2 hours one-way on a weekend without any stops, and if you carefully choose and plan which stops you want to make on your way to and from Portland, and are strategic with your time, you can definitely do it as a day trip. You could also just drive straight to Portland and spend all your time there.
Best Day Trip Itinerary For Boston To Portland, Maine
For a Boston to Portland, Maine day trip, I suggest trying to take this day trip in the summer when the days are longer, which will afford you more time to see as much as possible. But really, spring and fall are also a great time to take this trip (especially early spring when the days are also longer). Winter is the only time of year a day trip from Boston to Portland, Maine might be tough, since the days are so short.
Suggested Itinerary For A Day Trip From Boston:
Morning: Begin early, and drive to Ogunquit (about 1 hour and 20 minutes from Boston, depending on traffic). I suggest Ogunquit because chances are, if you live or are coming from Boston, you’ve already experienced nearby places like Salem and Newburyport. Ogunquit is further away, and likely not a place you’ve visited as often (or at all).
Late Morning: Leave Ogunquit and drive to Cape Elizabeth to see Portland’s lighthouses (Portland Head Light, Bug Light and Spring Point Ledge Light). If you only have time for one lighthouse, Portland Head Light is the one to see.
Afternoon: Drive into Portland, park your car for the day, and grab lunch. Spend the rest of your afternoon exploring Old Port, and if you have time, take the ferry to Peaks Island (best in the summer when days are longest).
Early Evening: Decide if you want to stay in Portland for dinner, or drive to Kennebunkport to explore that town for a bit, and grab dinner. If you stay in Portland, I would also suggest doing a beer tasting at one of Portland’s breweries, and maybe walking the Eastern Promenade around sunset. If you decide to head to Kennebunkport, the drive is only about 30-40 minutes from Portland.
Evening: Make your way back to Boston.
Best Time Of Year To Drive From Boston To Portland, Maine
Late spring and early-mid summer (so, June, July and August) are the best times to drive from Boston to Portland, Maine, simply because the weather is typically the nicest, and the days are the longest. Summer along the coast of Maine is just like anywhere in New England by the water – it comes alive. All the seafood shacks and ice cream places are open, and there’s a lively buzz in the air.
Fall is also a great time to take this drive because of the foliage and the pleasant weather. Just keep in mind that Maine tends to be a very seasonal state, as in many seafood shacks, as well as some restaurants and shops, will begin to close after Labor Day (most stay open through Columbus Day weekend, and some stay open year-round). But I’ve done this drive in early spring, summer and late fall and loved it just as much each time.
Boston in the fall is also lovely, so for a fall trip, it’s a great starting point.
Is There A Train From Boston To Portland, Maine?
Yes, the Amtrak Downeaster train provides service between Boston and Portland, Maine. The train ride typically takes about 2 hours and 30 minutes.
Is There A Bus From Boston To Portland, Maine?
Yes, the Greyhound Bus offers service between Boston and Portland, Maine. The bus ride takes about 2 hours and 30 minutes, and drops you off at the Park And Ride at Marginal Way in downtown Portland. From there, you can walk or Uber to your hotel or your next stop.
You may also enjoy reading:
- Incredible New England Resorts & Spas
- Best Boston Hotels Near The Aquarium
- Best Day Trips In New England
- Things To Do In New England For Your Bucket List
- 7 Day New England Road Trip Itinerary
- The Best Acadia National Park Itinerary
- Best Boston Food Tours
- Best Breweries In Portland, Maine
- Summer In New England: Places To Go & Things To Do!
- Fun Places For Blueberry Picking In Maine
- Maine In October: Best Towns For Foliage & Things To Do!
- Maine In November: What To Expect & Things To Do
That’s A Wrap On Driving From Boston To Portland, Maine
Now that you know how to plan the perfect road trip driving Boston to Portland, Maine, I hope you’ve begun to plan your own adventure! This is a great route to get acquainted with some of the best of coastal New England, and since it’s such an easy drive from Boston, it’s perfect for tailoring to your own schedule. Happy driving!