15 Best Things to Do In Portland Maine – Bearfoot Theory

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15 Best Things to Do In Portland Maine – Bearfoot Theory

Situated on the coastline of southern Maine, Portland is most known for being a quintessential New England city. With cobblestone streets, lobster

Situated on the coastline of southern Maine, Portland is most known for being a quintessential New England city. With cobblestone streets, lobster roll carts, lighthouses, a rich mariner history, and plenty of other attractions, Portland is definitely worth a stop on any New England road trip.

Don’t mind the fact that I don’t eat lobster (gasp!); this list is comprised of a ton of other best things to do in Portland, Maine including outdoor activities, must-visit sites, and delicious bites to eat (besides the seafood).

Note: this agenda is much better suited for folks visiting in the warmer months, as Maine is known to get some cold snaps and snow during the winter.

Take a Sunset Kayak Tour

The north end of the Portland peninsula juts out into the beautiful Casco Bay where Portland Paddle offers sunset kayak tours. The guided tour begins about 2 hours before sunset (check their website for an exact time when you go) and lets visitors enjoy the surreal beauty of the Maine harbor and marine life.

As of August 2022, the sunset tour is $45 per person and $40 for kids ages 10-16.

View out over front of kayak with Portland Maine skyline in distance and sunset skies overhead
Get the best seat for watching Portland’s famous sunsets on a guided sunset kayak tour

Walk, Run, or Bike Around Back Cove

Head a few minutes outside of the city by car or by foot to hike the 3.6 miles trail around Back Cove. It’s a paved and well-maintained pathway that offers beautiful city views and is great for kids or dogs on leash.

See What’s Happening at Thompson’s Point

Thompson’s Point is a waterfront venue with tons of events happening throughout the year. From a Summer Sunsets Live series to a Maker’s Market to open-air circus performances, there’s always something fun going on.

Check out the Thompson Point website for an updated event schedule. Spending a day or evening at Thompson’s Point is truly one of the best things to do in Portland, Maine!

Go Sailing on a Windjammer

One of the best ways to experience Portland, Maine is by sailboat. The Portland Schooner Co. offers two-hour sailing excursions on Casco Bay and beyond. It’s a great way to spend a morning and afternoon and see Portland from the water. Food and drinks are not included but passengers are encouraged to bring their own.

Tours are only available from May through October.

Sailboat on Casco Bay in Portland, Maine
See Portland from the water with a 2-hour sailing tour

Take a Surf Lesson at Higgins Beach

If the idea of surfing in Maine sounds crazy, think again — oh, and grab a wetsuit. Higgins Beach is a well-known New England surf break with pretty consistent waves year-round. It’s a popular spot with friendly locals and is located just south of the city near Cape Elizabeth.

Go to Black Point Surf Shop to rent a surfboard or book a lesson.

Hike the Fore River Sanctuary

From the center of the city, a short walk down Congress Street will get you to this 85-acre preserve with one of the area’s only natural waterfalls – Jewell Falls. Bring your dog, some friends, and a camera to snap photos of the beautiful marshlands and wildlife where the city meets the sea.

Give yourself a few hours to enjoy a leisurely stroll around this 3.2-mile loop — the golden hour is preferred.

>>Read Next: Best Hikes in Portland, Maine

Explore the Eastern Promenade

Local Mainers call this 2.1 miles of waterfront beaches and pathways “the prom”, which is easily one of the more desired areas of the city to live. It has a laid-back Venice Beach vibe with small bungalows and winding streets just a stone’s throw from the water. There is also a brewery on almost every corner, which makes it an easy shoo-in for my favorite spot on the peninsula.

Bring a towel and a picnic lunch and enjoy the small sliver of sandy beachfront and finish the day off with a drink at Lone Pine Brewing Co.

Camp on Richmond Island

Snag one of the four remote and primitive campsites available to visitors on Richmond Island just south of Portland and near Cape Elizabeth. This island gives you a unique beach camping experience that is totally off the beaten path and is one of the more adventurous things to do in Portland.

Before you head out, make sure you obtain a permit and bring your own firewood.

The island is only available by boat and there is no running water, no electricity, and no dogs allowed. As always, pack out all trash and tread lightly while exploring the area.

If you’re looking for more unique camping experiences, Wolfs Neck Woods State Park north of Portland is another of our favorites.

Eat, Drink, and Shop in Old Port

If you need a quick break from hiking, camping, and surfing, take some time to explore the Old Port District for a quintessential Maine experience. The city is full of creatives, makers, and entrepreneurs with super cool storefronts that are definitely worth a visit.

For eats and sips, check out Central Provisions which is tucked away on a cobblestone side street, and The Thirsty Pig, a fun place with good food and craft brews.

Cobblestone street lined with brick buildings in historic Old Port District of Portland Maine
The historic Old Port District is a great place for food and boutique shops

Stargaze at the Portland Observatory

The Portland Observatory is a fixture in the seacoast city and a symbol of its maritime roots. Trek up to Munjoy Hill to take a guided or self-guided tour of this historic landmark. You’ll be spoiled with panoramic views of the city and of course, a unique view of the ocean beyond the barrier islands.

The Portland Observatory on hill above houses and buildings in Portland, Maine
The Portland Observatory is a historic landmark that offers great views out over the city and waterfront

Take the Ferry to Peaks Island

Historically known as “The Coney Island of Maine” and a WWII outpost, a visit to Peaks Island is a unique stop for anyone visiting Portland. The ferry takes approximately 20 minutes (each way) and there are multiple departures per day. On the island, explore the Fifth Maine Museum, the world’s only Umbrella Cover Museum, and enjoy Lisa’s famous cinnamon buns at the Peaks Café. If you’re looking for something outdoorsy to do, you can also rent bikes and kayaks on the island.

Take a Self-Guided Craft Beer Tour

The city of Portland alone has over a dozen of breweries — some brick and mortar and some on wheels — that makes this Maine city a haven for beer lovers. Many of the breweries are located close to one another, so it is easy to do a self-guided walking tour, definitely one of the best things to do in Portland, Maine, in my opinion.

Downtown Portland Maine at sunset

Suggested route:

Begin at Austin Street Brewery on Fox Street, where they often have food trucks and events any day of the week. Right next door is Rising Tide Brewery, which has been in town for years and has a great reputation as a fun hangout with a large outdoor patio. Next, walk about seven minutes up Anderson Street to get to Lone Pine Brewing Co. Enjoy a pour-on tap before heading over to Goodfire Brewing Co., conveniently located next door.

While you’re in Portland, also check out these must-see breweries on the peninsula: Bissell Brothers Brewing Company, Oxbow Blending and Bottling, and Root Wild, a kombucha brewery with a few stellar beers on tap. The famed Maine Beer Co. is located 20 minutes north in Freeport and is worth a drive for diehard beer lovers.

If you want to join a guided tour, check out the Portland Brewery Tour with Maine Brew Bus.

Glass of beer etched with Maine Beer Company Do What's Right

Get Caffeinated at Tandem Coffee

You can’t go to Maine and not have coffee — not what you were expecting I would say, right? Well, it’s true. The line at Tandem Coffee runs out the door on weekends and for good reason, the coffee and baked goods here are outstanding.

So, get in line, and if the weather permits, hang outside where there is ample seating and a good vibe overall.

Visit the Portland Head Light

Portland Head Light is one of the most popular things to do for Portland visitors, but for good reason. The lighthouse is set on the rocky bluffs of Fort Williams Park, about 15 minutes south of the city in the town of Cape Elizabeth.

In addition to the historic lighthouse, the Park is also home to walking trails, an award-winning museum, several old forts, and a children’s garden.

Try to visit on a weekday, as this place does get busy.

Historic army ruins at Fort William Park in Portland, Maine
In addition to the lighthouse, Fort Williams Park is also home to historic army ruins

Visit the Portland Museum of Art

Located in the historic Arts District in downtown Portland, the Portland Museum of Art is a great place to spend an afternoon. With rotating exhibitions featuring a wide range of artists, there’s always something going on. Check the calendar for a list of upcoming events.

If you want to see even more art, time your visit to coincide with the free self-guided First Friday Art Walk.

What’s on your list of the best things to do in Portland, Maine? Did we leave anything out? Let us know in the comments!

Discover the best things to do in Portland Maine with this locals' guide including outdoor adventures best places to eat/drink, and more

Written by
Katherine Oakes

Katherine Oakes is an outdoor travel, sustainability writer and yoga teacher. As an avid hiker, skier, yogi (namaste) and aspiring environmentalist, her best days are spent getting a little dirt under her fingernails and fresh air in her lungs.

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