Cliffside strolls, fresh-off-the-boat seafood and thrilling water adventures are just three of the great ways for women to explore Portland, Maine, during a solo stay.
Why Portland Works for Solo Women Travelers
- Safe, walkable neighborhoods, scenic hikes and hands-on coastal experiences like lobstering and ferry rides that are ideal for women exploring solo.
- From lobster rolls to craft beer to Portland’s signature potato donuts, there’s a bite for every taste.
- Easy solo wandering through art galleries, museums, local markets and shops featuring authentic, locally made Portland goods.
The writer was hosted.
Things to Do in Portland on a Solo Adventure
Portland’s my go-to destination when I need me-time. Maine’s coastal jewel is an easy five-hour drive from my downstate New York home and delivers everything I look for on a solo spree: architectural eye candy, scenic walks to clear my head and fun things to do that my hubby doesn’t enjoy, like window shopping. He just doesn’t see the point. Men, right? Here are the top things to do on a solo stay in Portland, Maine.
1. Catch a Lobster
I hopped on board a lobster boat to learn the art of lobstering with the Lucky Catch Cruises team. Captain Tom and his crew motored us out into Casco Bay and let us try our hand at pulling traps. From July to November, Portland area lobster boats fish in the bay; in the winter, they need to venture farther out into the Atlantic.
It really is all about luck with lobsters. You bait the traps and push them off the boat. Then you check them in a couple of days, before the bait gets old and stinky. When retrieved, you hope to get at least one lobster that meets size requirements; they can’t be too small or too big. You can’t keep female breeders either. Yes. There are boy lobsters and girl lobsters. We learned to tell the difference. Girls have a wider tail and soft, thin, feathery swimmerets (the small legs under the tail)
SheBuysTravel: The Lucky Catch experience is featured in the Portland, Maine, episode of the Netflix series “Somebody Feed Phil.”
Are you ready to explore off the beaten path? Let us inspire you!
2. Take a Ferry Ride
Portland has an extensive ferry system that connects the islands of Casco Bay with the city. Operating for over 150 years, the Casco Bay Lines ferry service is based in a terminal in the Old Port District on Commercial Street. A popular option for visitors is to hop a ferry and take a day trip to explore Peaks Island, the most populated of the bay islands. The best way to get oriented is a 75-minute Spirit of Peaks golf cart tour.
3. All Aboard the Maine Narrow Gauge Railroad Co.
Take a ride on the Maine Narrow Gauge Railroad for scenic views of Casco Bay as you travel 35 minutes on a 3 mile long round trip. Trains leave every hour on the hour, beginning at 10 am, with the final trip at 3 pm.
4. Explore Portland’s Arts District
I get suckered in by art galleries everywhere I travel. While walking by, I’ll catch a glimpse of a painting or photo that I immediately fall desperately in love with. I wander in, saunter up to the object of my affection and, when I see the price, my heart breaks into a million pieces.
It happened to me again in Portland, but it didn’t stop me from popping into a number of galleries during my strolls. Art lovers should also check out the Portland Museum of Art.
5. Pick Up Blueberries and More at the Farmers’ Market
If you’re staying in an Airbnb or VRBO rental and need to stock your kitchen, a trip to the Portland Farmers’ Market is a must. It’s held twice a week, on Wednesdays and Saturdays, in Deering Oaks Park. It’s outdoors from May through November and indoors from December through April.
Visiting Portland in late summer? You’re in for a treat. That’s wild blueberry season in Maine. They’re small, sweet and delicious.
6. Wash Down Oysters with Craft Beer
If you drink beer, then you’re familiar with Allagash Brewing Company. Founded in Portland, the signature brew, Allagash White, is an easy-sippin’ Belgian-style wheat beer. Check out seasonal offerings in their beer garden. It’s located outside of town; depending on traffic, it can take you 45 minutes to get there, so plan accordingly.
Prefer to stay downtown? Head to the East End. You’ll find several craft breweries within walking distance of one another. Start at family-owned and operated Rising Tide. Their brews are created to pair with Maine’s cuisine. They suggest drinking their Daymark beer with local oysters. Then toddle over to Austin Street Brewery’s outdoor patio. Finish your tour at Belleflower Brewing, or, for a change of pace, try the rum at Three of Strong Spirits. Their small batch spirits use water from Maine’s Sebago Lake.
7. Climb to the Top of the Portland Observatory
There are a number of house museums in Portland to visit, including the Wadsworth-Longfellow House, home of the American poet Henry Wadsworth Longfellow (“Paul Revere’s Ride”), and the Victoria Mansion. If you only have time for one peek back in time, though, head to the Portland Observatory and take one of the guided tours.
The docent for my tour was an engaging senior citizen who led me up each of the 7 stories of the octagonal tower in the Munjoy Hill neighborhood. It was a journey the tower’s owner/operator Captain Moody made every day, including just before he died.
The Observatory functioned as a for-profit signal tower from 1807 to 1923. With a state-of-the-art telescope, scouts scanned the sea and sent notifications about approaching ships so that dock preparations could begin for unloading cargo. It is the only remaining signal tower in the United States.
8. Take a Seaside Hike
I walked off my many Portland meals by exploring the cobblestone streets between Congress and Commercial Streets—an easy, safe area for solo women travelers. Portland is a walkers’ city and the 2.1-mile Eastern Promenade offers well-trafficked paths and sweeping Casco Bay views.
For more exertion and ocean air, I drove 20 minutes to Scarborough Beach State Park, where on-site parking makes logistics simple. From the beach, turn right and follow the shoreline to the pumphouse; from there, take the Prouts Neck Cliff Walk. The full 4.3-mile loop features narrow cliffside paths with stunning sea views before transitioning into quiet residential streets lined with classic New England homes. The route is popular and well-marked—ideal for solo women seeking scenic but manageable trails.
SheBuysTravel Tip: For additional outings, Portland Trails sells maps on Commercial Street, and nearby Fort Williams Park offers a gentler wander to the iconic Portland Head Light.
9. What’s for Sale? Bags Made From Sails!
When traveling solo, I have a blast weaving in and out of the local boutiques. In Portland, that means wandering the cobblestoned Commercial Street district. It is NOT a vacation activity my hubby enjoys, so I made the most of my spree. If you want a legit “Made in Portland” souvenir, seek out the Sea Bags shop. The store’s tucked down a side alley on the harbor side of Commercial Street. It offers a variety of nautical waterproof bags, fashioned out of old sails.
10. Eat Your Way Around Town
Following are perennial palate pleasers to check out in Portland, 2018’s Bon Appétit’s Restaurant City of the Year. Expect long wait times at restaurants that don’t take reservations. Solo travelers can often skip the wait line and slide into bar seating.
- Scales: The large, bright dining room is located steps away from the ferry terminal. Start with fresh, local oysters. My lobster roll was the best of many I’d tried during our trip.
- Hot Suppa: Go for the chicken and waffles and thank me later. A popular brunch destination, Hot Suppa prepares the best Bloody Mary in Portland, according to my old college roommate.
- Eventide: Although it’s a tourist destination attracting large crowds, Eventide is worth a visit to sample the freshest oysters you’ll ever taste. Solo diners can sit at the bar and watch the shuckers do their thing.
- Highroller Lobster Co.: The lobster roll here features chunks of ocean-fresh lobster meat piled into a split-top roll. Choose a sauce, if you want to. They offer several flavored mayos. I chose to go old school and simply poured melted butter over the top. It was perfect.
- Holy Donuts: No visit to Portland is complete without a stop at Holy Donuts. The secret to the taste of these exquisite snacks? They’re made out of fresh Maine potatoes.
SheBuysTravel Tip: Don’t have time to try multiple restaurants during your stay? The three-hour Old Port Culinary Walking Tour provides a taste of the city’s flavors.
Where to Stay in Portland, Maine
Walkability matters when you’re exploring Portland on a solo trip. I suggest staying downtown, steps from the city’s attractions and renowned restaurants. Two Marriott-branded properties have different vibes and different price points. The writer in me was tickled by the lobby of the Press Hotel in Portland, one of Marriott’s Autograph Collection hotels. There are typewriters of all kinds on tables, desks and on the walls, an homage to the building’s history as a newspaper headquarters.
The Courtyard by Marriott features a thoroughly modern interior that makes this budget-friendly property feel luxe. Adding to its appeal is an extra-friendly staff. The front desk clerk was helpful with restaurant recommendations.
