13 Best Things to Do in Portland, Maine

The charming city of Portland, Maine, might be small, but it’s packed with character! Think working waterfront piers, cobblestone streets, historic lighthouses, and one of the best food scenes in New England, all wrapped up in a city that’s super easy to explore on foot.

We visited as part of our New England fall road trip and ended up loving how much there was to do in such a compact area. From sailing around Casco Bay to wandering through the Old Port, eating ridiculous donuts, and climbing to the top of a historic observatory, there was never a dull moment.

Whether you’re here for a weekend or just passing through, this guide rounds up the absolute best things to do in Portland, Maine – classic sights, local favorites, and a few food stops you really don’t want to miss!

*Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link.*

Best Things to Do in Portland, Maine

1. Walk around the Old Port District

The Old Port is the heart of downtown Portland and the first place you should explore when you arrive. This historic waterfront area is full of cobblestone streets, brick buildings, independent shops, seafood spots, and some of the city’s best cafes and bakeries.

It’s a great place to wander without an agenda. You’ll find everything from local bookstores and vintage shops to art galleries and boutiques selling all things Maine-made. The piers along Commercial Street are also worth checking out, and you can usually spot working lobster boats coming and going, especially in the morning.

If you’re planning to take a cruise or ferry, most of them depart from this area, so it’s easy to combine with other activities on the list. And if you’re into food, you’ll definitely want to come back here later in the day – it’s home to some of Portland’s best restaurants!

2. Visit Portland Head Light

No trip to Portland is complete without a visit to Portland Head Light. It’s the most iconic lighthouse in Maine (and one of the most photographed in the country) with a dramatic cliffside setting that looks straight out of a postcard.

You’ll find it in Fort Williams Park, about a 15-minute drive from downtown. You can’t get there by public transport, so it’s best to rent a car if you want to explore this area.

The lighthouse itself isn’t open for tours, but you can walk right up to the base, visit the small museum, and explore the surrounding park. There are numerous walking trails, stunning ocean views, and lush grassy areas perfect for a picnic.

We visited in the afternoon and spent about an hour here just taking in the views. If you’re hungry, there’s usually a Bite Into Maine food truck nearby serving up one of the best lobster rolls in town.

3. Check out the other lighthouses

Portland Head Light might get most of the attention, but there are a few other lighthouses around Portland that are well worth visiting. And the best part is that they’re all super close to each other!

Spring Point Ledge Light is a short walk along a granite breakwater, with great views back toward Portland Harbor.

Bug Light (officially called Portland Breakwater Light) is smaller but really photogenic, especially with the city skyline in the background. You’ll find it in Bug Light Park, which is also a nice place to relax or go for a short walk.

You can visit all of these on your own if you have a car, or you can join a guided tour if you’d rather not deal with parking or directions. This Portland City and Lighthouse Tour is a great option – it takes you to all the main lighthouses and gives a bit of local history along the way.

4. Explore Peaks Island

Just a 20-minute ferry ride from downtown, Peaks Island offers a quiet escape from the city with scenic coastal views, bike rentals, and a small-town vibe that feels a world away from the busy waterfront.

Once you arrive, you can walk around the island or rent bikes or golf carts to explore at your own pace. The 4-mile loop around the island takes you past rocky shores, quiet coves, and views of passing sailboats and ferries. It’s especially beautiful on a sunny afternoon.

There are a few restaurants and shops near the ferry terminal, but the real appeal is the slower pace and peaceful atmosphere. If you’re looking to see a different side of Portland without straying far, Peaks Island is an easy and fun half-day trip.

5. Sail around Casco Bay

One of the best things to do in Portland, Maine, is to get out on the water, and a cruise around Casco Bay is a great way to do just that! You’ll get views of the city skyline, several lighthouses, small islands, and if you’re lucky, maybe even some seals or harbor porpoises along the way.

There are a few different options depending on the vibe you’re going for. This Harbor Lights and Sights Cruise is a relaxed ride with plenty of lighthouse views, while the Tall Ship Cruise gives you the classic schooner experience under sail.

Whichever you choose, sailing around Casco Bay is a great way to take a break from walking and see Portland from a different perspective.

6. Join a food tour

Portland has a huge food scene for a city of its size, and one of the best ways to experience it is with a guided food tour. You’ll get to sample a variety of local flavors, like lobster rolls, chowder, sweets, and more, while also learning a bit about the city’s history and culture.

The Old Port Culinary Walking Tour is a popular option that takes you through some of the best bites in the Old Port. It’s a great way to try a little bit of everything without having to plan it all yourself.

If you’re into food-focused travel, this kind of experience definitely earns a spot on any Portland, Maine bucket list!

7. Eat a Holy Donut

If you’ve heard anything about Portland’s food scene, chances are someone has already told you to try a Holy Donut – and yes, they really are that good! These famous donuts are made with Maine potatoes, which gives them a super soft, almost cake-like texture.

They come in a bunch of fun flavors, from classic glazed to maple bacon, chocolate sea salt, and seasonal specials. We stopped by first thing in the morning, and the line was already forming, so try to go early for the best selection.

There are a couple of locations around Portland, but the one on Commercial Street is perfect if you’re already exploring the Old Port. Grabbing one (or three) is definitely one of the best things to do in Portland, Maine, especially if you have a sweet tooth.

8. Tour the Portland Museum of Art

Right in the heart of downtown, the Portland Museum of Art is one of the best cultural stops in the city. The collection includes works by big names like Monet, Picasso, and Andy Warhol, along with pieces by Maine-based artists like Winslow Homer and Andrew Wyeth.

The museum is fairly compact, so it’s easy to explore in an hour or two, and the layout is clean and modern. If you’re visiting on a Friday, admission is free between 4 pm and 8 pm, which is a nice bonus if you’re trying to fit a few things into one day.

Even if you’re not a huge art person, it’s a calm and quiet break from the busier parts of downtown and a good add-on to any Portland itinerary.

9. Visit the Wadsworth-Longfellow House & Longfellow Books

This historic home belonged to poet Henry Wadsworth Longfellow and is one of the oldest brick houses in Portland.

You can take a self-guided tour through the rooms, which are filled with original furniture and personal items from the Longfellow family. It’s a quick stop, but a fascinating glimpse into Portland’s past.

Right next door is Longfellow Books, a cozy indie bookstore that’s perfect for browsing after your visit. It’s packed with a great mix of new releases, local authors, and staff picks, plus it’s just a nice place to slow down for a bit before heading back out to explore.

10. Walk along the Eastern Promenade

If you’re wondering what to do in Portland, Maine, that doesn’t involve food or museums, head to the Eastern Promenade. This scenic, waterfront park stretches along the edge of Casco Bay and offers great views, a paved walking path, and plenty of space to relax.

It’s especially nice in the morning or late afternoon, when the light hits the water just right. You’ll see locals out jogging, walking dogs, or just hanging out on the benches with a coffee. If you want to extend your walk, you can follow the Eastern Prom Trail all the way to Back Cove.

It’s a peaceful change of pace from downtown and a great spot to take in the coastal vibe without leaving the city.

11. Visit the Victoria Mansion

Just a few blocks from the Old Port, the Victoria Mansion offers a totally different side of Portland – one that’s all about 19th-century elegance and over-the-top interiors. The mansion was built in the 1850s as a summer home and is one of the best-preserved examples of pre-Civil War architecture in the country.

Inside, you’ll find ornate woodwork, original furnishings, and ceiling murals that look like they belong in a European palace. It’s a guided experience, and the staff do a great job of bringing the history to life without it feeling overly formal.

If you’re into historic homes or architecture, it’s an easy add to your list of things to do in Portland, Maine – and a nice break from the more modern parts of town.

12. Climb to the top of the Portland Observatory

The Portland Observatory is the last standing maritime signal tower in the US, and climbing to the top is one of the most unique things you can do in the city. It was built in 1807 to spot incoming ships and still offers some of the best views in Portland today.

The climb is short but steep (about 100 steps), and you’ll pass through several levels with exhibits on local history and seafaring along the way. At the top, you’re rewarded with panoramic views of the city, Casco Bay, and even the mountains on a clear day.

It’s only open seasonally, usually from late May through early October, so check opening times before you go.

13. Go brewery hopping

Portland has one of the highest numbers of breweries per capita in the US, so if you’re into craft beer, this is the place to be! You’ll find everything from hoppy IPAs and sours to stouts, lagers, and seasonal brews – all within a short distance of each other.

Some of the most popular spots include Bissell Brothers, Allagash, Rising Tide, and Austin Street, but there are plenty of smaller breweries worth checking out, too. Many have outdoor seating and rotating food trucks, especially on weekends.

If you want to sample a few without worrying about driving or planning your own route, consider booking a guided tour like the Portland Pubs Walking Beer Tour. It’s a fun and easy way to try several places in one afternoon and learn a little about the local brewing scene along the way.