10 Fun Things To Do In Portland, Maine
Your Guide to the Top Sights, Flavors And Outdoor Experiences
By Lissa Poirot | Published on December 9, 2025
Perched on Maine’s rocky coast, Portland, Maine, is one of the cities that wins visitors over instantly. It’s small enough to feel friendly and walkable, yet filled with the kind of coastal charm and creativity that put Maine on travelers’ radars. Cobblestone streets lead to working wharves, seafood shacks sit beside art galleries and the scent of saltwater mixes with the aroma of freshly baked whoopee pies.
This New England gem is also one of the most rewarding stops on a Canada and New England cruise itinerary. Within minutes of stepping ashore, you can visit historic lighthouses, sample lobster straight from the dock and discover why Portland’s craft breweries have earned national attention.
Here are 10 fun things to do that showcase the best of Portland, from its famous Old Port to its scenic shoreline and local flavors.
Top 10 Fun Things To Do In Portland, Maine
1. Explore Old Port
The heart of downtown Portland, Old Port is a mix of 19th-century brick warehouses, cobblestone lanes and the buzz of a working harbor. Just steps away from the pier, it’s the perfect first stop to stretch your legs and take in the city’s maritime vibe and one of the best things to do in Portland, Maine on a New England cruise.
Browse boutiques filled with nautical décor and Maine-made crafts, or grab a lobster roll and watch fishing boats unload their catch. The district stays lively all day with coffee shops, ice cream parlors and waterfront restaurants serving up fresh oysters and local ales. If you only have a few hours in town, Old Port captures the spirit of Portland in one compact area.
2. Visit Portland Head Light
Arguably Maine’s most iconic landmark, Portland Head Light has stood guard over the Atlantic since 1791. Set within Fort Williams Park in Cape Elizabeth, it’s about a 20-minute ride from the city center, and completely worth the trip.
Clifftop walking paths wind along the rugged shoreline, offering postcard-perfect views of crashing waves and rocky coves. You can tour the small museum inside the former keeper’s quarters or enjoy a picnic on the park’s rolling green lawns.
3. Take A Lobster Boat Tour
Nothing says “Maine” like lobster, and in Portland, you can experience the state’s signature catch up close. Lobster boat tours are a fun thing to do in Portland, Maine, with kids; they depart from the waterfront and take you into Casco Bay, where captains haul traps, explain the ins and outs of sustainable fishing and share stories of life on the water.
The tours are educational but also fun, with chances to see seals and seabirds along the way. Some operators even offer tastings so you can try a freshly cooked lobster roll right on deck.
4. Walk The Promenade Trail
Stretch your legs and soak up the sea air on the Eastern Promenade Trail, a scenic path that hugs Casco Bay for about two miles. The route passes picnic areas, small beaches and panoramic viewpoints that capture the beauty of Portland’s coastline is one of the top family things to do in Portland, Maine.
It’s easy to walk from downtown or rent a bike for a breezy ride along the water. In the fall, fiery foliage colors frame the bay in reds and golds, turning the trail into one of Maine’s best spots for seasonal scenery.
5. Eat At A Classic Lobster Shack
If there’s one thing you must do in Portland, it’s sampling the city’s legendary seafood. Maine’s lobster shacks are simple but unforgettable, serving lobster rolls piled high with tender meat on buttery toasted buns.
Order the “Connecticut style” with warm butter or the “Maine style” with mayo and lemon. Pair it with clam chowder and a whoopee pie, the official state dessert.
6. Visit The Portland Museum Of Art
The Portland Museum of Art, home to works by American artists like Winslow Homer and Andrew Wyeth, is an airy, light-filled space that celebrates Maine’s creative spirit. European pieces and modern exhibits are also featured.
You can easily explore the museum in an hour or two, making it a great option for a rainy day, but rain or shine, don’t miss the sculpture garden.
7. Tour The Wadsworth-Longfellow House
For a step back in time, visit the Wadsworth-Longfellow House, the childhood home of poet Henry Wadsworth Longfellow. Built in 1785, it’s Portland’s oldest standing structure and offers fascinating insight into early American life.
Guided tours reveal original furnishings, personal artifacts and stories about the Longfellow family. Outside, the formal garden is especially lovely in spring and summer.
8. Hop The Casco Bay Ferry
If you have a few extra hours, take to the water aboard the Casco Bay Lines ferry. Short routes connect Portland to nearby islands like Peaks Island, known for its laidback vibe and beachy charm.
Once there, you can rent a bike to circle the island, browse tiny art galleries or enjoy ice cream by the shore. The ferry ride itself is a mini cruise past lighthouses, lobster buoys and sailboats that dot the bay.
9. Shop The Portland Farmers’ Market
One of the oldest markets in the country, the Portland Farmers’ Market dates back to 1768 and continues to thrive today. Held in Deering Oaks Park on Wednesdays and Saturdays, it features local produce, flowers, baked goods and handmade crafts.
It’s a wonderful place to mingle with locals and pick up edible souvenirs like blueberry jam or maple candy. Even if you’re not shopping, it’s worth a visit just to stroll beneath the towering oak trees and enjoy a true slice of Portland life.
10. Sample Local Breweries
For a city of its size, Portland boasts an impressive number of craft breweries – more per capita than almost anywhere else in the U.S. Unsurprisingly, one of the top things to do in Portland, Maine, is to sample a brewery. Beer lovers can easily spend an afternoon sampling everything from crisp lagers to inventive sours.
Start with Allagash Brewing Company, famous for its Belgian-style ales, then check out Bissel Brothers, Shipyard or Rising Tide closer to the downtown area. Many breweries offer tours, and several pair their pours with lobster rolls, pretzels or other local bites.
Planning Your Day In Portland, Maine
With so many highlights packed into a small, walkable area, Portland is one of the easiest New England ports to explore in a single day. Most visitors find they can experience a wide mix of food, scenery and sightseeing without feeling rushed, especially because Old Port and many top attractions are within walking distance of the cruise terminal.
Old Port is the natural starting point with its waterfront setting, cobblestone streets and boutiques you can browse the moment you step ashore. For attractions slightly farther out, like Portland Head Light or breweries on the outskirts, a short taxi or rideshare trip will do the trick.
If you plan to take a ferry or lobster boat tour, schedule those experiences early in the day to leave time for exploring downtown later. Most cruise passengers find they can comfortably fit two or three activities into their port call without feeling pressed for time.
Best Time To Visit Maine
Maine shines in every season, but cruise passengers will find the months between late spring and early fall offer the most comfortable conditions and longest days for sightseeing. June through August brings reliably warm weather perfect for boat tours, lighthouse visits and waterfront dining.
Fall is considered one of the best times to visit, with vibrant foliage, cooler temperatures and fewer crowds compared with peak summer. For many cruisers, this season delivers the best combination of scenery and atmosphere.
Weather Tips
Portland’s weather changes with the wind, literally. Summer days are typically mild and sunny with temperatures hovering in the mid-70s F. Even then, sea breezes can cool the waterfront quickly, so packing light layers is key, especially if you’re planning to walk the Eastern Promenade or visit lighthouses right on the shoreline.
Comfortable shoes are essential for navigating Old Port’s uneven cobblestones and the short cliffside trails at Fort Williams Park. Spring and early summer can bring morning fog that lifts into clear skies, while late-day temperature swings are common year-round.
If your cruise arrives in late September or October, expect crisp air and some of the most colorful foliage in New England. This is one of the most rewarding times to explore Portland’s outdoor spaces, from lighthouse overlooks to wooded paths and waterfront parks.
