If you’re planning a trip to Maine’s largest city, you’re in for such a treat — Portland is absolutely packed with coastal charm, incredible food, and beautiful lighthouses. From its working waterfront and cobblestone streets, to its arts scene and ocean views, there’s such a wonderful mix of things to do when you visit.
I’ve visited Portland countless times over the years, in all four seasons, in fact. I’ve explored all the well-known attractions and the little hidden gems that make it special, and I’m here to help first-timers navigate the city. I’ll show you what’s most worth focusing on during your visit to make the most of your time, so you can create a pretty memorable itinerary.
So, let’s dive in – here are the very best things to do in Portland, Maine!
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Can’t-Miss Things To See & Do In Portland, Maine
1. Explore Old Port – The City’s Most Charming Area
Old Port is by and far the city’s most charming and picturesque area. Located in Portland’s downtown region, Old Port sits along the waterfront, and is home to working wharves, charming cobblestone streets, shops, and restaurants.
This neighborhood has roots dating back to the 1630s, believe it or not! But there was a large fire that more or less demolished the area, and most of what you see today is from the rebuilds that took place in the mid to late 1800s.
Old Port is incredibly walkable, and it’s easy to stroll along the waterfront, pop into the shops, and plan a nice lunch or dinner out – all within a couple of hours. It’s quaint, but definitely packs a punch.
While walking around Old Port, I recommend walking down the Pier at Luke’s Lobster to enjoy the water views and old, working ports. Then heading over to Commercial Street, which runs along the water, and where you’ll find some cute shops and such. Then, head up Dana Street to pass by the picturesque, ivy-covered Via Vecchia restaurant, and pop down Wharf Street to take in the cute little alley. Enjoy the shops along Fore Street before heading to the cute little Exchange Street area.
2. Take A Drive To Portland’s Lighthouses
The city’s lighthouses are definitely something you want to see during your visit, and offer such a nice contrast to the bustling downtown. Located in South Portland and Cape Elizabeth, they’re only about a 15-20 minute drive away (depending on traffic), and have those iconic Maine coastal views you’re probably hoping for.
If you only have time to see one of the lighthouses, be sure it’s Portland Head Light. This is the most famous and photographed lighthouse in New England, and one of the most famous in the U.S. It’s picturesque setting along the dramatic, rocky coastline makes it such a memorable experience, and you can enjoy different viewpoints of it along the coast walk around the park.
Pro Tips: Portland Head Light is located inside Fort Williams Park, and there’s a fee to park, but the grounds are free to walk around. However, the lots are fairly large, and you can pay via a credit card at the kiosks. The Bite Into Maine food truck is often open at the lighthouse, which means you can enjoy a really good lobster roll with views of the lighthouse for a perfect afternoon experience. If you’ve seen photos of people out on the rocks in front of the lighthouse, it’s good to know that they’ve since locked the gates, and access to those areas is no longer allowed. However, there are still amazing photo opportunities of the lighthouse from tons of different angles.
The lighthouse that’s furthest south is Cape Elizabeth East Light, which also technically has a sister – Cape Elizabeth West Light. However, these lighthouses are both privately owned and not accessible. That said, you can get a nice view of Cape Elizabeth East Light from the beach at Dyer Cove. There’s a public lot there at the end of Two Lights Road (just park right where it ends at the beach), and enjoy the quintessential Maine scenery – which includes views of the lighthouse.
I also really love Bug Light, which has a funny name, but it’s actually a beautiful and uniquely ornate lighthouse that’s worth seeing. It’s fairly small, but it’s distinctive design makes it memorable to visit, and it’s situated inside a nice little park that you can enjoy during your time there.
Lastly, there’s Spring Point Ledge Light, which is also worth your time. This is another small lighthouse, but you can walk out onto the rock jetty to reach the lighthouse, which is a fun experience that allows you to get close to it and enjoy the water views from a different perspective.
If you have the time to see all the lighthouses, I really do recommend it. They’re all very close to one another, and each one offers a unique experience, making them all special in their own way. You can easily visit them all in 3-4 hours.
3. Dive Into Portland’s Incredible Culinary Scene: Restaurants, Bakeries & More!
Portland is regularly regarded as one of the most exciting culinary destinations in New England, as well as the entire U.S. I don’t think I’ve ever had a mediocre or disappointing meal in Portland, and your problem will actually be narrowing down where to eat because the options seem endless.
Of course, seafood dominates menus in Portland, and places like Scales, Eventide, and Luke’s Lobster are all fantastic places for a great seafood dinner. Luke’s is the more casual of these options.
For creative spots, you’ll want to check out Isa Bistro, Via Vecchia, Fore Street Restaurant, and Central Provisions.
Of course, you don’t want to skip yummy treats! In fact, Portland is home to a bakery that was rated as one of the best in the entire country: Standard Baking Co. This one is located in Old Port, so it’s easy to get to when staying in this area, and they make absolutely amazing pastries, including croissants, tarts, cookies, brownies, and so much more. During my most recent fall visit, I had an apple cake that was seriously to die for here.
You also don’t want to skip the famous Holy Donut, which were made famous by making their donuts from potatoes, which offers a more dense and rich texture. They have various flavors that change seasonally, and every one I’ve ever gotten has been awesome.
I also really love Bread & Friends, which has amazing croissants, lattes, chai, and they sometimes also have pop tarts – so if you see those in their bakery case, just go ahead and snatch that up. They’re so good. My husband also loves their brown butter pumpkin spice latte in the fall season.
For some casual dining suggestions, I really love Cheese Louise and Flatbread. Cheese Louise is a grilled cheese place with a few locations around New England. And honestly, this place is perfection. Their tomato soup is also fantastic, and I also really enjoy their maple-infused lemonade.
Flatbread is a wood-fired pizza place that also has a few locations around New England, and the pizzas here are wonderful. They’re located right on the waterfront in Old Port.
I also really love Green Elephant Vegetarian Bistro. This is a cozy spot for Asian fusion, and as the name suggests, everything is vegetarian (and since my husband is vegetarian, we eat here a lot when in town). We came here on our first-ever visit to Portland many years ago, and the quality has never changed. Their asparagus tempura salad and roti starters are so, so good, as is everything else on their menu.
Lastly, while in Old Port, I recommend heading into Gorgeous Gelato, which has incredible gelato, but other fun things like a really good hot chocolate, affogato, Italian coffee, and more.
All that said, you kind of can’t go wrong with most dining choices in Portland. There are so many restaurants to choose from, and lots of up-and-coming chefs who are earning Michelin stars. If you’re a foodie, you’ll definitely want to have a game plan for your visit when it comes to dining, and make reservations ahead of time!
Bonus Suggestion: Take A Food Tour!
If choosing where to eat sounds overwhelming (and don’t worry, I still get overwhelmed trying to decide here to eat in Portland after so many visits đŸ˜‚), you can opt for a food tour.
This walking food tour of Old Port is a great way to get out with a local guide who gives you a wonderful look into the city’s culinary scene, all the while sampling dishes from six different places. You’ll want to come hungry, as this tour is enough food to replace a meal – if not more.
→ Click here to check out this Old Port walking food tour with a local expert
4. Explore Casco Bay On A Tall Ship
Being that Portland is a coastal city, it would be a shame to not get out onto the water. I’ll have a few suggestions in this post on how to do that, but one really memorable option is cruising along Casco Bay in a tall ship.
This tall ship cruise is a lot fun, and you’ll spend two hours sailing along the water to enjoy a completely different perspective of Portland. The crew even encourages you to help hoist the sails, or take a turn at the captain’s wheel for an extra special experience – but you can also just sit back and relax if that’s what you’re looking for.
→ Click here to check out the tall ship cruise in Portland
5. Enjoy All The Impressive Breweries
In addition to being an exciting culinary destination, Portland is also known for having the most breweries per capita in the entire U.S., which means there’s stiff competition, raising the bar in terms of quality for craft brews. If you love a good brewery, this is something you’ll want to carve out some time for during your visit.
There are over 60 breweries in the city, and I don’t think a single one my husband and I have tried has been bad. Some of our favorites include Belleflower, Bissel Brothers, and Austin Street. However, I have a whole post on our favorite breweries in Portland, Maine, after having visited quite a few of them over the years. That post will definitely point you in the right direction đŸ˜‰
6. Pop Into Batson River For Awesome Cocktails
Baston River has a few locations in Maine, including one in Portland, and they’re known for their gorgeous interiors and fantastic cocktails. While they also brew their own beer, I really think the cocktails are more worth checking out during your visit.
They also serve a full food menu for both lunch and dinner, so you can dine here as well. I usually just have a seat at their beautiful bar and to sip on their cocktails, though, which makes this a fun place to visit for pre-dinner drinks.
They often have rotating seasonal cocktails that evoke the flavors and mood of the moment — making every visit a wonderful experience that feels perfectly in tune with the time of year.
7. Stroll The Beautiful Eastern Promenade & Midslope Trail
Located right in the heart of downtown Portland, you can easily pick up both of these trails, which are gorgeous and easy coastal walks. The Eastern Promenade is about 2.1 miles long (round trip) flat path that starts near the Maine Narrow Gauge Railroad (which I’ll talk about in a bit đŸ˜‰) and ends in the East End. It’s such a lovely walk to enjoy more secluded waterfront views in the city.
However, I actually personally prefer the Midslope trail, which takes you up to Fort Allen Park, and follows the Eastern Promenade from a higher elevation. You can either walk to Fort Allen Park to start this trail, or you can begin on the Eastern Promenade, and look for the staircase through the woods, which you’ll take up to the park. This staircase can be found at 43.66437416735339, -70.24026727109585, and you’ll just cross the railroad tracks to find it. It’s very easy, and there will be a sign.
This part of the trail has a lovely gazebo at the park, and if you continue heading northeast on the trail, you’ll pass by lovely views of the Promenade from above, beautiful coastal views, and eventually, stumble upon a community garden. This garden is such a hidden gem in the city! Please just admire and don’t touch while there, but definitely enjoy it.
At the garden, walking closer to the water, you’ll see a little frame set up against the backdrop of the bay, which makes for a really fun photo opp. You’ll also get wonderful views of East Portland from this spot.
I also prefer this trail because you have the option to enjoy the houses in the East End that sit along the main road on Eastern Promenade Rd.
You can’t go wrong with either trail, however, and both have wonderful views and beautiful scenery.
8. Cruise Casco Bay On The Ferry
Another fantastic and more affordable option to get out on the water during your visit in by hopping aboard the Casco Bay Ferry line. These ferries go to various nearby islands, and you’re welcome to use them as a cruise option just to experience the city from the water.
Single passenger rates vary from $7-$14 as of 2025, depending on the type of year (summer season is usually more expensive). And these prices are for round-trip tickets.
The most popular route is the Peaks Island route, which is actually my next suggestion below, so be sure to check that out. This usually takes about an hour total, and is very easy to squeeze into a shorter trip (although, best to check the current schedule, especially if you’re short on time). However, you can head to some of the other islands if you’re looking for a longer trip.
9. Head To Peaks Island
So, speaking of Peaks Island, this is actually a really fun place to explore if you have a longer stay in Portland planned (I’d suggest at least two full days to work this into your itinerary). This little island is only 3 miles off the coast of the city, and is such a great little spot to feel like you’ve traveled quite far. You’ll find a more relaxed vibe on the island, but still tons of coastal Maine scenery that’s worth making the effort for.
At only about a mile wide at its longest point, Peaks Island is very easy to explore with just a few hours, or a half day. To maximize your time, you can even rent a golf cart or bike on the island to make it easier to get around. Peaks Island Golf Carts is just a few minutes by foot from the ferry terminal on the island, and you can also take a 5-6 minute walk to Brad & Wyatt’s bike rentals.
10. Take A Ride On The Maine Narrow Gauge Railroad
Located near the start of the Eastern Promenade trail, the Maine Narrow Gauge Railroad is a really cool way to explore the city.
The trains run on 2-foot-wide tracks, which is a much narrower gauge than the standard U.S. width of 4 feet. It was originally designed in the late 1800s to reduce construction costs and navigate Maine’s rugged terrain. Today, the 40-minute scenic tours travel along Casco Bay, offering beautiful coastal views and a nostalgic experience.
The trains have both open-air and covered cars, and they have frequent departures throughout the day seasonally from May through the end of October. In the winter, they open back up for the holidays to run their very fun Polar Express train rides.
11. Learn All About Lobstering With Lucky Catch Cruises
Finally, one last way to get out onto the water while visiting Portland is by taking a lobstering adventure around the bay.
Lucky Catch offers an authentic hands-on experience that allows you step right into the life of a local Maine lobsterman. During the 80–90 minute cruise, visitors help haul traps, learn how to bait them, and discover interesting facts about Maine’s lobster industry, as well as sustainable fishing practices. You’ll also take in iconic coastal Maine views, passing lighthouses and islands along the way.
At the end of each tour, guests can even purchase the lobsters that were caught during the tour at “boat” price, and if you take them across the pier to Portland Lobster Co., they’ll cook them up for you to eat at the restaurant for a memorable experience.
Where To Stay In Portland, Maine
I always recommend that first-time visitors stay in Old Port, which is centrally-located in the city, and you’ll be able to walk to a lot of places. Having stayed in various parts of the city, I can confirm that Old Port is truly the best area to stay in, and the most convenient. You’ll also find a selection of the best hotels in this part of the city. All of these suggestions are in Old Port.
The Press: Part of Marriott’s Autograph collection of hotels, The Press is definitely one of the best hotels in the city. The hotel has a very boutique feel, and is incredibly well-designed for a more upscale experience.
→ Click here to check rates & availability for The Press hotel
Portland Harbor Hotel: A nice mid-range option that feels a bit like a boutique hotel experience. Rooms have been recently renovated, and they also have a cool fire pit on their grounds.
→ Click here to check rates & availability for the Portland Harbor Hotel
Hyatt Place Old Port Square: I stay here a lot because it’s a great mid-range hotel in such a convenient location. Rooms are pretty standard, but perfect for a little getaway, and you’re steps from everything in Old Port. If you have the World of Hyatt credit card, you can also use points for your stay.
→ Click here to check rates & availability at the Hyatt Place Old Port Square
Visiting Portland, Maine: Answering Your Questions
How Walkable In Portland?
Portland is a very walkable city when you’re in the downtown/Old Port area. However, if you want to get to the lighthouses, you’ll need a car to drive there. When you’re exploring downtown, you can leave your car parked all day.
Is Portland Expensive To Visit?
It can be, yes, and it depends on the season. Portland’s high season is June through early September, and this is when all hotels will be expensive, and when you’ll experience the most crowds. However, the tradeoff is that you get the best weather. The fall season will bring slightly lower prices at hotels, but prices don’t begin to fall significantly until after the holiday season.
Winter is the off-season in Portland, and this is the cheapest time to visit (January-March/early April).
What’s The Best Time Of Year To Visit Portland?
Personally, I really love late October in Portland, which is when the city’s foliage is typically at peak. Portland is such a cozy city, and when combined that with all its fall vibes, it really adds to your overall experience with falling leaves, beautiful autumnal colors, and bundling up with sweaters and scarves.
The downside to visiting in late October is that some boat tours are closed for the season, so if you’re really hoping to get out onto the water, and have your pick of tours, you may want to visit June through mid-October. That said, the ferry lines are open year-round.
Does Portland Make A Good Base For Exploring Maine?
Absolutely! But only if you’re looking to focus on southern Maine. The state is fairly large, so getting to places like Acadia National Park, for example, is not realistic as a day trip from Portland. That said, you’ll be within an hour’s drive to Ogunquit, Kennebunkport, York, and Freeport, and then you can also get to Boothbay Harbor in just over an hour.
If you’re looking to explore more of Midcoast Maine, you’ll probably want to break up your trip with some time in Portland, and then book an additional stay somewhere like Rockland or Camden. If you want to get to Acadia, it’s best to plan at least a night or two in Bar Harbor or one of the nearby towns on Mount Desert Island.
More Posts You May Enjoy:
- My Perfect Maine Lighthouse Road Trip Itinerary
- Incredible Stops To Make Between Portland, Maine & Acadia National Park
- Best Places For A Maine Vacation
That’s A Wrap On Can’t-Miss Spots In Portland, Maine
And there you have it – my ultimate guide on all the top things to do in Portland, Maine that you don’t want to miss as a first-time visitor. Whether you’re heading to the city for a day trip, or planning a little weekend getaway, there’s truly so much to do for a relaxing yet exciting trip. Happy planning!
