FinancialWize

Fall in Portland, Maine is a spectacular experience, filled with vibrant colors and a host of activities. September to October is the best time of year to enjoy the magic of fall in Portland, from the scenic coastal views to fun downtown festivities. Stroll through the charming streets of the Old Port, where you can explore local shops and enjoy seasonal treats at cozy cafes. Don’t miss the chance to visit nearby orchards for apple picking or take in breathtaking views on a scenic drive. With local festivals celebrating food, art, and community, there’s fall things to do in Portland, ME for everyone to enjoy. 

Whether you’re searching for a house to rent in Portland, ME, an apartment to call home, or ready to purchase your first home in the city, , this city has so much to offer. Let’s explore 15 fall things to do in Portland, ME, where pops of color and cozy vibes create the perfect backdrop for autumn and give you a taste of why Portland is a good place to live.

1. Pop some tags at the local thrift shops

The community around thrift and vintage shopping in Portland is eclectic and supportive, hosting regular events like swap meets and pop-up markets. Whether you’re hunting for a vintage vinyl record, mid-century furniture, or stand-out fashion statements, you’ll be sure to find something unique at one of Portland’s thrift stores.

“One of my favorite things about Portland is the amount of thrift and vintage shops we have,” shares local photographer Shado of Shado of a Rose Photography. “All within a 10-minute walk you could get incredible vinyl at Moody Lords, find that new sweater you need for fall at Material Objects, or pick up a retro video game/movie poster from Electric Buddhas.”

And, if you’ve worked up an appetite while thrifting, Shado has you covered. ”If you’re in the mood for some food just pop over to Exchange street a few blocks away. Whether you’re getting incredible chicken from Crispy Gai, eating $1 oysters on a Wednesday night at Blyth and Burrows, or having dessert at Gorgeous Gelato, you really can’t go wrong when going out in the Old Port.”

2. Admire the fall foliage in Portland

Whether you’re walking, biking, or simply taking a drive, enjoying the fall foliage in and around Portland is a perfect way to experience the changing of the seasons. The contrast of the colorful foliage with the historic architecture and coastal scenery creates a picturesque setting that feels like a scene from a postcard.

Fall colors around town

“This small East Coast city, with its cozy New England town feel, offers a little bit of something for those wanting to feel at home or someone seeking a temporary home base to do some leaf-peeping in Maine during the fall season,” describes local Portland author Marpheen Chann.

One of the best ways to experience the fall foliage in Portland is by exploring the many parks and waterfront areas. “A walk or bike ride on smooth trails can take you around Back Cove, where you can get a quality photo of Downtown Portland from across the water at Payson Park. Continue your day at Portland’s Eastern Promenade, the perfect place for a picnic with scenic views of Casco Bay and its islands,” Chann shares.

Catch a train

You can also relax into a scenic tour of the fall foliage by hopping on the Maine Narrow Gauge. “From your comfortable seat on the historic train, take in the dazzling colors of autumn, set against the backdrop of Casco Bay. You’ll hear all about Portland’s history and learn about local landmarks from onboard narration,” describes Matt Levy, general manager of the Maine Narrow Gauge Railroad. You can also get special Pumpkin Train tickets for the last two weeks of October, and continue the fun into the holiday season with a Polar Express themed train ride. 

Finish the day

Hungry after a day of exploring fall in Portland? “Experience some of Portland’s iconic and diverse restaurants without the summer crowds with Cambodian-Chinese eats at Oun Lidos on Market Street,” recommends Chann. “If you’re looking for a good spot for a drink or a casual date, pickup where you left off with a friend or a book at Novel on Congress Street or snag some downtown views high up at the Top of the East on High Street.”

Whether you’re walking around town or getting into the countryside, experiencing the fall colors in Portland is an autumn must-do – finished off with great food, of course.

3. Wander the picturesque streets of Portland

“Portland in the Fall is magical,” gushes Adria Moynihan Rusk, a painter at Still Life Studio in Portland. “You’ll skip the rush of summer tourists while being here at the most picturesque time of year. Check out the Old Port and Bayside neighborhoods to find a unique selection of local shops and breweries.”

Old Port

Portland’s neighborhoods offer a mix of maritime heritage and urban appeal, inviting you to spend your autumn days wandering their streets. “Fall is a perfect time to explore Portland,” agrees Sierra Bisson, author of the travel blog The Ocean Drifter. “Walk around the cobblestone streets of the Old Port, where you’ll find great shopping and amazing restaurants.”

Charming lanes and narrow alleys wind through the Old Port, where brick buildings house eclectic shops, art galleries, and cozy restaurants. “When you’re in the area, make sure to stop by must-try spots like Duckfat and Taco Escobarr,” Bisson continues. “If you’re in the mood for some nightlife, swing by Bonfire for a fun evening with a great atmosphere and drinks.” 

The Waterfront

If you’re looking for places to stop by on your stroll, Rusk is full of suggestions. “Grab a latte at Bard Coffee and walk down Commercial Street to people-watch along the waterfront,” she shares. “Take the fairy out to Peak’s Island and back, and then head to Washington Avenue for a hot bowl of Pho Ga at Cong Tu Bot. Don’t forget to try the potato donuts at the Holy Donut.”

To finish off your day of exploring Portland in the fall, Rusk recommends, “Find a park bench on the East End promenade and watch the boat traffic skip across Casco Bay. It’s hard to do it wrong, so make an adventure of it.”

4. Warm your insides with local beer tasting

Portland, ME’s craft beer scene is renowned for its creativity, quality, and variety, making it one of the top destinations for beer lovers in the country. The city boasts a high concentration of breweries, from long standing favorites like Allagash Brewing Company to newer, experimental breweries like Bissell Brothers. Many breweries are located in Portland’s industrial areas and waterfront, offering taprooms where guests can sample a range of styles, from hoppy IPAs and smooth stouts to crisp lagers and sour ales.

“You absolutely have to check out at least one of the local breweries – Portland is known for its craft beer scene,” confirms Bisson of The Ocean Drifter blog.

Must-visit breweries

“Fall in Portland isn’t complete without attending Oktoberfest at one, or more, of the city’s great breweries,” seconds local tech expert and beverage connoisseur Dan DeSimone. “I especially like Belleflower, which is walking distance from a number of other breweries like Austin Street and Rising Tide. Tandem Coffee is right down the street too if you’re in the mood for a latte break (pumpkin spice optional) between beers.”

The East Bayside is another area that is renowned for its breweries, with local chocolate shop Dean’s Sweets offering the perfect neighborhood map to plan out your day of beverage sampling. “The East Bayside is one of the fastest-changing neighborhoods in Portland, ME,” reveals Kristin from Dean’s Sweets. “There are spirit makers, food trucks, hard seltzer, and cider right alongside the many breweries and wineries. And of course, chocolate at Dean’s Sweets, for those who want a gift for others or a nibble for yourself,” she laughs.

Join a beer tour for a unique beer-tasting experience

For a fun way to spend fall in Portland and sample the craft beer scene, consider a beer tour. “Join the Maine Brews Cruise for a cozy, festive journey through Maine’s craft alcohol scene amidst the backdrop of stunning fall foliage,” shares the Maine Brews Cruise team. 

With options of a guided walk through the streets of Portland or having your own designated driver on a tour bus, the Maine Brews Cruise is perfect for those who enjoy a snug atmosphere while exploring local breweries, distilleries, and wineries. “With expert guides and a warm setting, you can learn, taste, and toast to the season – flannel attire recommended for the full autumn experience,” says the team.

You can also embrace Portland’s coastal vibe with a beer and boat tour through SeaPortland. “For those eager to experience Portland’s crisp fall beauty and rich history, SeaPortland provides exclusive tours that combine sightseeing with local brew tastings,” describes the crew. “You can explore historic Fort Scammel or enjoy a Harbor Cruise, where the vibrant fall colors enhance the flavor of each locally brewed beer. These 90-minute tours promise a blend of good vibes and spectacular sights, ideal for anyone looking to savor the season.”

However you prefer to indulge in the local craft beer scene, the city’s community-focused beer culture is a great fall thing to do in Portland.

5. Get outside into Portland’s local landscape

Portland is a mix of coastal beauty and historic urban charm. Located on a peninsula overlooking Casco Bay, the city’s waterfront features working harbors, marinas, and scenic parks like the Eastern Promenade. In the fall, the vibrant foliage adds to the town’s allure, making outdoor exploration a must.

See the scenery

“Visiting Portland in the fall is many people’s highlight of the year,” states Nick Robinson of Portland Schooner Co. “For a nature experience in town, try the walking trails at the Evergreen Cemetery where you can catch migrating birds in the trees, turtles and other amphibians in the ponds, and an array of tree species lighting up the landscape with their vibrant colors.” 

You can also get a new perspective of Portland’s scenery via a historic wooden schooner, sailing your way around Casco Bay on the Maine-built boat through the Portland Schooner Co. “Don’t forget your hat, sunglasses, and cozy layers,” reminds Robinson.

Enjoy your dining outdoors

“Autumn in Portland is my favorite time of year,” confesses Chelsea K Ray, a wardrobe consultant and blogger based in the city. “Breakfast right on Casco Bay at the Porthole is a must. Walk off your lobster Benedict with a stroll along the East End Trail, and don’t forget to dip your toes in the ocean at East End Beach.”

Ray recommends doing some shopping at Mexicali Blues and Ports of Call on Commercial Street before enjoying fresh seafood at DiMillos, a floating restaurant that features beautiful waterfront views. “Wrap your day up with a cocktail at the Commercial Street Pub,” encourages Kay, noting that the pub is a true local’s spot where you can share your day’s adventures with other patrons.

6. Celebrate the season with Harvest on the Harbor

Since its inception in 2007, Harvest on the Harbor has celebrated Portland’s outstanding culinary scene, showcasing the talents of local chefs, brewers, distillers, and food artisans. “This is the 16th year for Harvest on the Harbor, which draws attendees from around the world to savor the deliciousness of Maine,” shares the Harvest on the Harbor team.

Portland has earned the reputation as “The Foodiest Small Town in America,” and the festival nods to this title by highlighting Maine’s rich food and beverage culture. 

“Harvest on the Harbor is a celebration of Maine-made spirits, Maine lobster, Maine oysters and Maine seafood,” confirms the team. “With four events in three days there is something for everyone, including the Maine OysterFest, From The Sea and the Maine Cocktail Classic.”

Held the last weekend of October, Harvest on the Harbor offers a fun fall outing and a tasty celebration of Maine’s local flavors and traditions.

7. Indulge in Portland’s fall flavors and festivities

Portland celebrates fall with festivals, outdoor markets, food, and events like the Portland Farmers’ Market, which overflows with fresh produce, baked goods, and seasonal flowers.

Local eats and treats

“Portland is simply vibrant in autumn,” affirms Jamie, author of the blog Travel Addict. “Whether you are tasting local beers at the Portland Beer Hub, hiking on Peaks Island, or tasting the freshest of seafood along the waterfront, it’s the perfect fall destination with something for everyone. The cuisine is top notch – with incredibly fresh seafood at Scales and exquisite flavors at Duck Fat.”

Seasonal favorites like cider donuts, craft pumpkin ales, and hearty farm-to-table dishes become staples at eateries across the city, making a food tour a perfect fall thing to do in Portland.

“Maine Day Ventures keeps you moving and learning while you eat and shop,” suggests Kristin of Dean’s Sweets. “The guide gives an insider’s behind-the-scenes taste of the most popular spots in the city. The tour includes generous portions of some Maine specialties, including lobster, blueberries, craft beer, and the always-loved Maine potato, along with some up-and-coming foodie trends.”

Fall activities

Other fun fall activities come recommended from the Harvest on the Harbor team, including visiting corn mazes, hiking, trying award-winning restaurants, shopping and gallery hopping. 

“Every Friday, the City of Portland hosts a First Friday Art Walk with gallery openings,” says Harvest on the Harbor. “Performing arts opportunities include the Portland Symphony Orchestra, celebrating its 100th season with performances at a few area breweries and a pay-what-you-can Chamber Series.”

8. See the city by sea

Experience Portland by sea for stunning views of Casco Bay, its islands, and iconic lighthouses like Portland Head Light. Fall tours provide a quieter, more intimate experience, with crisp air and warm autumn sunlight reflecting off the water.

“If you’re looking to enjoy Maine’s autumn spectacle, Casco Bay Custom Charters offers cozy flannel-wrapped adventures aboard vintage vessels,” shares Dyland Suhr from Maine Tour Company. “Enjoy breathtaking views of the colorful coastline with a bottomless mimosa brunch or a sunset dinner prepared by a private chef. This is the perfect opportunity for private groups to make unforgettable leaf-peeping memories on the water.”

Charter a boat for an intimate and private experience, or take the ferry across the bay to Peaks Island for a day of strolling amongst the neighborhood’s fall colors.

“Catch the ferry at Casco Bay Lines,” recommends Kristin from Dean’s Sweets. “The 30-minute trip across the bay is fun all on its own. Get some sun and enjoy the sparkling water and cool air along the way. If you’re lucky, you may see a bald eagle or a harbor seal.”

9. Take a day for everyone to play

“A trip with loved ones to Portland wouldn’t be complete without a visit to the Children’s Museum & Theatre of Maine, the state’s most visited museum and top destination for play located at Thompson’s Point,” says Shultzie Fay Willows, a representative for the museum. 

Kids can explore hands-on exhibits like water and air activities, an outdoor playground, and an indoor climbing structure. They can also enjoy cultural displays, aquarium tours, performances at the country’s oldest children’s theater, and creative activities in MakerSpace – all included.

To round out the fall weekend in Portland, Willows is full of all-ages recommendations. “Afterward, paint some pottery next door at Color Me Mine or explore the fascinating International Cryptozoology Museum,” she shares. “For lunch, stop by Bissell Brothers, savor a grilled cheese at Sacred Profane, or enjoy hot dogs and pierogi at Leisure Time. There is something for everyone to do, try, and explore.”

10. Journey to the countryside for a true fall farm experience

A 40-minute drive from Portland, Bowdoinham comes alive in autumn with apple picking, pumpkin patches, and hot cider. This rural town along the Kennebec River is known for its vibrant farming community and fall harvest season.

If you’re looking for beautiful colors, Stonecipher Farm is an organic farm brimming with bright veggies in the autumn months. “The ‘no-till’ approach to vegetable production means a highly organized field system, resulting in an outstanding aesthetic,” claims Ian Jerolmack from the farm. “Folks have said it looks like the king’s garden.”

When you’re done exploring the farm, head back into town and sample from many other local farms at various Bowdoinham fall festivals, where vendors line up with their fresh offerings and handmade crafts.

11. Bring Fido along for the adventure

Portland is known for being an exceptionally dog-friendly city, welcoming four-legged companions in many public spaces and businesses. Numerous restaurants and breweries have outdoor patios where dogs are welcomed with water bowls and treats. The city’s pet-friendly vibe extends to shops, where many local businesses allow well-behaved dogs.

“There are many restaurants and locations that are dog-friendly throughout the city, just make sure to check their pet policy and local leash laws to ensure you and your dog have a great and safe time enjoying Maine’s fall together,” advises Portland pet photographer Gina Soule.

“Enjoying Portland in the fall alongside your four-legged best friend gives you a taste of the very best of Maine,” Soule continues. “From having your dog join you for a stroll along the Eastern Prom, exploring Higgins beach together, to enjoying an adult beverage around a fire on the patio at Maine Craft Distilling, you can’t go wrong with any of the numerous dog-friendly locations Portland has to offer.”

12. Cozy up with a good book

Fall and books are the perfect pair, whether you’re curling up in a chair by a roaring fire or sipping on tea at a local cafe with a book in hand. “Portland has a rich and robust bookish culture, with tons of amazing bookshops throughout the city,” adds Ash Holland, local owner to The Lucky Fox Bookshop.

Local favorites include Sherman’s, which opened in 1896, residing as Maine’s oldest bookstore. Another is Longfellow’s, a classic book shop with the perk of having the occasional feline guest wandering the store, available to adopt if it happens to choose you.

But if you’re after a fun and unique bookshop experience, look no further than The Lucky Fox Bookshop. A traveling and online bookstore, The Lucky Fox is an independently-run business that hosts pop-up shops at hot spots around Portland, and centers their collection around LGBTQ themes, fantasy, and works from marginalized authors. “Check out the event page to see where we’ll be setting up shop this fall and winter; or, explore the online shop to snag your next great read,” advises Holland.

As the weather gets cooler, many bookstores also host special events like author signings, book clubs, and seasonal sales, making bookshop hopping a perfect fall activity for a day in Portland. 

13. Prepare to be spooked at a haunted house

A visit to a haunted house perfectly captures the fall mood, blending eerie history with spooky entertainment as the days grow shorter and colder.

While there are multiple haunted houses you can explore around Portland, nothing quite beats The Annual Haunting at the Parsonsfield Seminary. Originally built in the 1800s, its 42 rooms transform into an epic spooky mansion for the ultimate Halloween experience. You’ll be led on a tour through the building’s four floors for a suspenseful storytelling show, guaranteed to give you some scares. Tours are offered only the last two weekends of October, and the seminary changes its act every year for a truly unique time.

While the Parsonsfield Seminary is located an hour out of Portland, it’s more than worth the trip. Make a weekend of it by staying nearby with Backcountry Excursions, where owner Cliff Krolick ensures you get the full fall experience cozying up in one of his yurts or cabins nestled within the woods.

14. Travel off the beaten path on an oyster tour of Portland

“If you’re an oyster lover visiting Portland, be sure to check out the Maine Oyster Trail,” recommends Trixie Betz, an oyster expert. 

The Maine Oyster Trail, of which Portland is a major hub, offers activities like farm tours, boat tours, raw bars, shuck trucks, and even kayaking adventures, where you can see oyster farming up close and taste the product directly from the source. It’s a great fall activity that combines education, fresh seafood, and Maine’s scenic coastline​. 

“Fall is the best time to enjoy oysters, and what better place to do that than in Maine,” shares Betz. “Not only will you enjoy delicious Maine oysters and learn about the industry, you’ll earn prizes along the way.”

The Maine Oyster Tour includes an oyster passport you can use to keep track of the places you’ve visited; the more establishments you check into, the more prizes you earn. The farm-to-table approach of the experience gives you the unique opportunity for direct interaction with Maine’s oyster farms, making the Maine Oyster Trail a perfect fall thing to do in Portland.

15. Escape the chill with local nightlife

Portland’s nightlife changes with the seasons, especially in the fall when outdoor patios stay open with heaters and fire pits. Many places also host seasonal events, from Halloween-themed parties to fall harvest festivals that go into the night. Rising Tide Brewing Company and Oxbow Blending & Bottling have both indoor and outdoor spaces, and you can often find live music or food trucks. 

For local music and laid-back vibes, check out the Flask Lounge for nightly live music, dancing, and up-and-coming DJs and bands. “Nestled in the heart of Portland, Flask Lounge is your favorite down-to-earth neighborhood bar,” affirms Flask Lounge owner Jessica Nolette. “Known for its unassuming charm and the city’s most affordable drinks, it truly feels like home.”

If dancing isn’t your thing, cozy up inside an intimate cocktail bar instead. The Portland Hunt + Alpine Club will serve you creative drinks in a sleek, Scandinavian-inspired space. For a warm and vintage vibe, Blyth & Burrows features a speakeasy-style experience, with handcrafted cocktails celebrating the maritime history of Portland. 

Whether you’re in the mood for craft beers, live music, dancing the night away, or a more elegant evening, exploring the nightlife in Portland fall will leave you feeling warmer than you started.

Discovering fall things to do in Portland, Maine

There’s truly something special about fall in Portland, Maine. From festive farmers’ markets to cozy cafes and autumnal events, there’s something for everyone to enjoy. Whether you’re a lifelong resident or a first-time visitor, there are a plethora of fall things to do in Portland just waiting to be discovered. So bundle up, head out into the brisk air, and immerse yourself in all the fall fun this enchanting New England city has to offer.

Source: rent.com