A fishing village turned adventure paradise, Portland is home of Maine’s largest port. Here you’ll find equal parts paddlers and lobstermen exploring Casco Bay and the outlying islands. But Portland is not just a water town (although surfers go at it year-round). New Hampshire’s White Mountains are within striking distance, as are three ski resorts.

“There are few places in the world where you can wake up in the morning, have a leisurely cup of coffee, load your car and Thule roof rack or box, and in two hours or less be rockin’ just about every adventure sport you can think of,” says Portland local John Connelly. “Not to mention the incredible beer.”

Meet the expert: John Connelly, 57, has lived on the border between Portland and Falmouth for almost 20 years. A former member of the U.S. Whitewater Kayak and Canoe Team, Connelly is currently co-founder, president, and chief experience officer of Adventurous Joe Coffee LLC.

Hike: The nonprofit Portland Trails maintains a network of more than 30 trails throughout the Portland area. Choose the Presumpscot River Trail—featuring singletrack and wooden bridges—to follow the river and ditch the crowds.

Ride: The East Coast Greenway Trail, extending from Maine to Florida, runs through Portland on its way south. Try a section of it by taking the Amtrak Downeaster train from Portland to Wells, Maine. Then bike the Eastern Trail (a mix of off-road and country roads that is part of the East Coast Greenway) 35 miles back to the train station in Portland. “Refuel at the Great Lost Bear,” Connelly suggests. “It’s one of America’s best brew pubs with more than 70 taps. And it’s just a mile from the train station.”

Climb: The Portland Head Light, a lighthouse on the craggy coast, is a fun local bouldering spot (up to V4), and has climbing on the cliffs up to 5.12.

Ski: For cross-country, Pineland Farms is 30 minutes away. For downhill, travel an hour to Shawnee Peak in Bridgeton, known for its night skiing and family vibe. Or go 1.5 hours to Sunday River Ski Resort, one of the East Coast’s best ski resorts with double black diamond runs like White Heat and challenging glades.

Paddle: Put-in downtown at East End Beach and paddle over to Back Cove or into Casco Bay to Peaks Island. “If you paddle to Peaks, be sure to go to the Inn and get a Portland-made microbrew from Shipyard Brewing Company,” Connelly says.

Surf: Higgins Beach and Scarborough Beach State Park, pristine sand beaches with consistent breaks, can be found 20 minutes south of Portland. An hour to the north is Popham Beach State Park, with a vast beach and different exposures to open ocean offering right and left breaks. “At the right tides, long rides are a feature here,” Connelly says.

Locals’ favorite adventure: In nearby Falmouth, the Class IV Presumpscot River falls are always runnable. Plus, they are virtually unknown—most visiting whitewater paddlers journey north to the Class IV–V Kennebec and Penobscot Rivers.

Something visitors don't do but should: Hike and float down the Presumpscot in the summer at high tide. Wear your bathing suit under your clothes and bring a dry bag. Leave one car at the Walton Park parking lot in Falmouth, and drive the other upstream to the Presumpscot River trailhead at the Gray Road bridge just north of Portland. Hike the riverside trail roughly 1.5 miles downstream to the falls. Put your clothes and shoes in the dry bag, jump in, and float downstream in the current. Use your dry bag for support and keep your feet up. After passing beneath the Allen Avenue Extension Bridge, climb out on the all-tide dock on river left at Walton Park where you left your car. Hang out at the swimming float and soak up some sun with the locals.

Where to eat: Pre-adventure—Bintliff's American Café for breakfast or brunch. Or grab something quick from Bernie's Foreside in Falmouth, Bruce's Burritos in Yarmouth, or Marcy's Breakfast & Lunch in Portland. Post-adventure, head to Novare Res Bier Café in the Old Port district downtown, or Sea Dog Brewing Company. Feeling brave? Try Silly's, with dishes you’ve never had (or heard of) and an eclectic vibe. For a bit more elegance, go to the Front Room Restaurant and Bar, the Grill Room & Bar, or the Corner Room Italian Kitchen & Bar restaurants. For foodies looking to drop coin—Fore Street, Hugo's, or Street and Company. “Don't miss Eventide Oyster Co. for an epic oyster experience, including oyster shooters,” Connelly says. “And be sure to grab one of their curbside tables on Fore Street.”

Where to imbibe: Great Lost Bear, Novare Res Bier Café, Gritty McDuff’s Brew Pub, Sebago Brewing Company, In'finiti Fermentation & Distillation on the waterfront.

Where to stay (budget): Recompence Shore Campground at Wolfe's Neck Farm in Freeport, or the Maine Island Trail, where camping is free for members. Join and choose any one of the many islands with campsites in Casco Bay.

Where to stay (splurge): The Portland Regency Hotel & Spa in Portland's Old Port.

39 Places to Have a Great Long Weekend

Master the three-day weekend getaway in one of these vibrant adventure towns across the United States. With the advice of a trusted local, discover the best spots to hike, bike, paddle, eat, drink, and sleep.