Portland is Maine's largest city, and you won't easily run out of activities to occupy your time, but when you do, these day trips will satisfy your sense of adventure. Whether you're looking for outdoor recreation or art museums, outlet shopping bargains or unique galleries and boutiques, beaches or historic sites, or even a driving tour, you'll find plenty to entice you within a short radius of Portland.
Freeport: Shopper's Heaven
The L.L. Bean flagship store is famously open 24/7/365, making Freeport, Maine, a destination not just for shopping-addicted daytrippers but for night owls, too. The L.L. Bean campus is home to Discovery Park, where events including a free summer concert series are held. Surrounding Maine's legendary retailer, you'll find more than 100 other shops including factory outlets from brand names like Vineyard Vines, Calvin Klein, and Cuddledown.
But Freeport isn't just shopping. The town also offers uncrowded beaches, a tidal river teeming with wildlife, a working fishing harbor, a desert, and Wolfe's Neck Woods State Park with broad views of Casco Bay from rocky beaches and high bluffs.
Getting There: Freeport is a 20-minute drive north of Portland on I-295. If you prefer to use public transportation, METRO BREEZ bus service between Portland and Freeport is comfortable and affordable, or hop aboard the Amtrak Downeaster for a relaxing ride on the rails. For more information, check out our full article on how to get to Freeport from Portland.
Travel Tip: When you're ready to take a break from shopping, the Tavern Lunch Buffet at Freeport's Harraseeket Inn is one of the best all-you-can-eat values in New England.
Rockland: Maine's Arts Hub
If the Portland Museum of Art's rich collection inspires you to seek out even more art treasures, then plan a day trip to the coastal city of Rockland. The Farnsworth Art Museum and its Wyeth Center showcase American works including famous scenes painted by the prominent Maine family of artists: N.C., Andrew, and James Wyeth. Serious Wyeth fans can also tour the Olson House, famously depicted in "Christina’s World," a half-hour away in Cushing, Maine. Rockland's Center for Maine Contemporary Art, opened in 2016, will beckon to you with its exhibitions of work by the best living artists with ties to Maine, displayed in a Toshiko Mori-designed building.
Getting There: From Portland, drive north on I-295, then follow Route 1 through historic and scenic towns like Bath and Wiscasset, and you'll be in Rockland in just over an hour and a half. Alternatively, you can take a Concord Coach Lines bus between the two cities for $40 round-trip.
Travel Tip: While in Rockland, walk atop the granite wall that leads to Rockland Breakwater Light. The Maine Lighthouse Museum is in Rockland, too, so you may want to consider staying over and making this a two-day trip.
Salem: Witch City
Salem's dark history, which stems from the witch trials of 1692-1693, gives this seaside city north of Boston a distinct aura. Top attractions like the Salem Witch Museum and The Witch House offer visitors a glimpse of the hysteria that gripped the settlement and its horrible repercussions. The spooky fun reaches its peak in October, when the city hosts a month-long slate of Haunted Happenings. Salem has a less campy side, too, with attractions like The House of the Seven Gables that celebrate its literary heritage and the Salem Maritime National Historic Site, which tells the story of Salem's seafaring past. The eclectic art on view at the Peabody Essex Museum fascinates visitors, too.
Getting There: Salem, Massachusetts, an hour and 40 minutes from Portland in the car via I-95 South to Route 128 North to Route 114 East. Public transportation is difficult but possible. It requires taking a bus or the Amtrak Downeaster train all the way to Boston, then switching to a local bus or train to Salem.
Travel Tip: If you're visiting Salem with kids during the warm-weather months, they'll love the old-school arcade and amusements at waterfront Salem Willows Park. Buy the big bag of popcorn at E.W. Hobbs: it'll be the best you've ever tasted.
Gloucester: America's OG Seaport
Like Portland, Gloucester is a harbor town, but its rough-and-tumble character is distinct in all of New England. Gloucester isn't just America's oldest fishing port: It is still very much a working fishery made even more famous as the filming location for the National Geographic TV program, "Wicked Tuna." Fill a day in Glouchester touring Hammond Castle, popping in and out of artist studios on Rocky Neck, and touring Cape Pond Ice, which manufactures the ice used aboard the city's fishing vessels. Gloucester is also home to wonderfully scenic beaches, and, of course, the seafood is as fresh as can be.
Getting There: The drive time between Portland and Gloucester is just under two hours: Follow I-95 South to Route 128 North. Public transportation requires taking a bus or the Amtrak Downeaster train to Boston, then switching to a local bus or MBTA train to Gloucester.
Travel Tip: If watching whales in the wild is on your bucket list, Gloucester is a great place to spot them. Two companies, Cape Ann Whale Watch and 7 Seas Whale Watch, guarantee sightings (or a future trip is free).
Peaks Island: Simple Pleasures
For an inexpensive escape, Portlanders head to Peaks Island. Hop aboard the Casco Bay Lines ferry to Peaks Island in just 17 minutes you're on an adorable isle where you can set out to explore on foot or on a rented bike. The beaches here are uncrowded, as is the island's quirky Umbrella Cover Museum. Even if you just make the crossing to have lunch and ice cream, you'll feel like you've enjoyed a daycation with Portland in view.
Travel Tip: Sit back and relax on a golf cart, and allow Peaks Island Tours to show you this 720-acre island.
Moultonborough: A Castle and a Realm of Adventures
Home to Castle in the Clouds and Riding in the Clouds—where you can ride horseback or take a horse-drawn carriage ride—Moultonborough, New Hampshire, is a perfect day trip destination on Lake Winnipesaukee. In addition to self-guided castle tours and equestrian opportunities, the quirky former estate of self-made millionaire Thomas Plant offers 28 miles of hiking trails and dining with a spectacular view of the lake and mountains at the Carriage House Restaurant. Moultonborough is also home to the Loon Center and Markus Wildlife Sanctuary, where a walk along the Loon Nest Trail allows you to view a nesting pair of loons from late spring through early fall.
Getting There: You'll get to enjoy a scenic drive of about an hour and 40 minutes on Route 25 getting to Moultonborough.
Travel Tip: Be sure to stop into the oldest store in the country while you're in Moultonborough to buy snacks and souvenirs.
Sebago Lake: Freshwater Fun
The second-largest lake in Maine is also one of its deepest and clearest. That makes Sebago Lake State Park and its beaches a perfect place to cool off on a summer day. This 28,771-acre lake in Casco and Naples, Maine, is also a popular spot to fish for lake trout, bass, perch, and other species. Boating of all sorts is an option, too. Year-round, The park's trails are open year-round to hikers and in the winter to snowshoes and cross-country skiers.
Getting There: Enjoy a picturesque drive on Route 302 northwest from Portland to Sebago Lake State Park.
Travel Tip: Want to ensure you'll see a moose while you're visiting Maine? Detour to the Maine Wildlife Park in Gray, open mid-April through mid-November, on your way to Sebago Lake.
Portsmouth: New England Past and Present
The city that brands itself "A Tiny Bit Huge" is just across the Piscataqua River from southern Maine. A day visit to Portsmouth will give you a taste of this historic port city that will leave you wanting to return. Settled in 1623 and remarkable for its preserved architecture and waterfront attractions like the living history museum Strawbery Banke, Portsmouth is a picture-perfect New England city at the intersection of what's vibrant and new and what's old and still cool. Foodies, beer fans, and shopaholics will love browsing the town's independent boutiques and galleries.
Getting There: From Portland, follow I-295 South to I-95 South to Portsmouth: It's about an hour's drive. Greyhound bus fare between the two coastal cities is about $20 one-way.
Travel Tip: On your return drive to Portland, make a stop at the outlet stores just across the Piscataqua River Bridge in Kittery, Maine.
Georgetown: Drive to an Island
One of the Maine coast's best-kept secrets, the island of Georgetown is super-accessible (it's connected to the mainland by a bridge), but it feels like a world all its own. Spending a day here means walking the beaches at Reid State Park, feasting on lobster with an idyllic view at Five Islands Lobster Co., shopping for locally made Georgetown Pottery, and maybe even staying late to hear live music at the landmark Robinhood Free Meetinghouse.
Getting There: Head out of Portland driving north on I-295, and take exit 28 onto Route 1 toward Brunswick and Bath. Turn right in Bath onto Route 127 South, and cross the bridges that connect Arrowsic and Georgetown islands to the mainland. Total drive time is just about 45 minutes.
Travel Tip: As you drive through Bath, you'll get a glimpse of Bath Iron Works, founded in 1884 and still a major builder of ships for the U.S. Navy.
Denmark, Naples, Poland, Paris, China: A World Tour Without Leaving Maine
If you want to explore Maine on a drive, make a game of finding Maine towns with names inspired by faraway places. Start out from Portland on Route 114 North, and set your GPS first for Denmark. Next up: Naples. Then Poland and Norway. In Paris, Maine, there is no Eiffel Tower, but you can dine at Maurice Restaurant Francais. Hungry for more? Continue to China and Palermo before looping back south to Portland. This is one adventure you can even enjoy without ever leaving your car.
Getting There: Your GPS is your globetrotting best friend on this day trip: Use it to navigate from destination to destination. If you drive the entire "world tour," you'll be in the car for about five-and-a-half hours without stops. Shave two hours of drive time off the route by returning to Portland after you see Paris.
Travel Tip: If you skip China and Palermo, you'll return to Portland via Route 26 South and pass by two unique Maine attractions you may want to add to your itinerary: Sabbathday Lake Shaker Village and the Maine Wildlife Park.