Local’s Guide: 12 Fun Things to Do In Portland Maine

Plan an adventurous trip with these things to do in Portland Maine! This bucketlist will get you outdoors, exploring town & finding the best places to eat/drink.

12 THINGS TO DO IN PORTLAND MAINE

by Bearfoot Theory’s East Coast expert Katherine Oakes

After soaking up all the outdoor (and indoor) adventuring that the city of Portland, Maine has to offer, my tiny family and I decided to stop talking about how, “we could totally live here” and just, well, live there already. It’s an exciting move for sure since the seacoast has more than its fair share of outdoor activities, amazing food, secret spots and an all-around great vibe that would have anyone coming back for more.

Don’t mind the fact that I don’t eat lobster (gasp!), this list is comprised of a ton of other things to do in Portland Maine, places to see and delicious bites to eat besides the seafood. It’s also worth mentioning that this agenda is much better suited for folks visiting in the warmer months, as Maine is known to get some cold snaps and snow.

Check out this local’s guide for some of the best things to do in Portland Maine.

1) 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 trip 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. It’s $40 per person, $35 for kids ages 10-16. Book a tour on their website.

Plan an adventurous trip to Portland, Maine! Here are 12 things to do in Portland that will get you outdoors, exploring town & finding the best places to eat/drink.

2) 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.

3) Thompson’s Point

Year-round events from Summer Sunsets at the Point, to a Pop-Up cycling class, or a live show featuring some of Portland’s best local bands make for a good time at this waterfront location. Check out their website for their updated event schedule.

4) 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 for $45 per person — drinks are not included but encouraged. The tours are only open from May through October so make sure you book your tour during the season.

Plan an adventurous trip to Portland, Maine! Here are 12 things to do in Portland that will get you outdoors, exploring town & finding the best places to eat/drink.

5) Surf Lesson at Higgins Beach

If the idea of surfing in Maine sounds crazy, think again — oh and grab a wetsuit. This New England locale is a well-known surf break with pretty consistent waves year round.  It’s a popular spot with friendly locals that is just south of the city near Cape Elizabeth. Go to Black Point Surf Shop to rent a surfboard for just $35 and a wetsuit for $25. You can also book a 90-minute lesson with them for $80 a person or $140 for two people.

6) 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. 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. If you’re looking to spend more time outdoors in Maine, make sure to check out our favorite things to do in Acadia National Park.

7) 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 in. It’s a got a laid-back, Venice Beach vibe, with small bungalows and winding streets just a stone’s throw from the water, plus a brewery on every corner that made it a shoe-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.

8) 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 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 or dogs allowed. As always, pack out all trash and tread lightly while exploring the area! Remember to leave no trace when camping. Check out this page for instructions for securing a camping permit.

Plan an adventurous trip to Portland, Maine! Here are 12 things to do in Portland that will get you outdoors, exploring town & finding the best places to eat/drink.

Photo from Ramislandfarm.com

Don’t forget any of the essentials with our backpacking checklist

9) 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. Some of my favorite finds were More & Co., Maine Surfers Union and Judith Maine. As 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.

Plan an adventurous trip to Portland, Maine! Here are 12 things to do in Portland that will get you outdoors, exploring town & finding the best places to eat/drink.

10) Stargaze at the Portland Observatory

The observatory is a fixture in the seacoast city and a symbol of its maritime roots. Trek up to Munjoy Hill to take a tour of the waterfront landmark and you’ll be spoiled with panoramic views of the city and of course, a unique view of the ocean beyond the barrier islands. Admission for adults is $10 and $5 for children ages 6-16.

11) Take a self-guided brewery tour

The city alone has nearly 20 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… that is, until, you know, walking gets a little hard towards the end and sitting down for dinner is a much better plan.

Try walking this route: Begin at the newest brewery in town: 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, who has been in town for years and have a great reputation as a fun hangout with a large outdoor patio, perfects for bringing your dog. Afterwards, walk about seven minutes up Anderson Street to get to Lone Pine Brewing Co., the only brewery in town that allows you to bring dogs inside. Enjoy a pour on tap before heading over to Goodfire Brewing Co., conveniently located next door.

While you’re here, 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.

Plan an adventurous trip with these things to do in Portland Maine! This bucketlist will get you outdoors, exploring town & finding the best places to eat/drink.

12) 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. ‘Cause you’re gonna need some caffeine to fuel all your adventures, might as well power up here.

What are your favorite things to do in Portland Maine?

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About the author

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.

3 Comments on “Local’s Guide: 12 Fun Things to Do In Portland Maine

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  1. Great post. Articles that have meaningful and insightful comments are more enjoyable, at least to me. It’s interesting to read what other people thought and how it relates to them or their clients, as their perspective could possibly help you in the future.

    I also enjoyed your shared all these fabulous fun things during my last journey of this awesome destination and we came back with smiley faces.

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