Things To Do

Giant's Stairs Trail

Named for its interesting geologic history, the Giant’s Stairs trail follows the rocky coastline with gorgeous views of eastern Casco Bay, often with crashing waves glinting in the sunlight. On any given day you might see rafts of ducks, foraging harbor seals, or a lobster boat hauling traps.

Cliff Trail

Cliff Trail is one of the most popular trails in Harpswell. The main loop, Cliff Trail, is 2.3 miles and marked in white blazes. The shorter Cut-off Trail is marked in yellow blazes. This trail features an inclusive .4-mile shore walk along tidal Strawberry Creek with a nice view of the cascade and a resting area.

Devil's Back Trail Area

Devil's Back Trail is a scenic and popular hiking area located in Harpswell, Maine, offering visitors a unique outdoor experience. This trail is renowned for its stunning coastal views, rugged terrain, and diverse natural surroundings. As you hike along Devil's Back Trail, you'll encounter rocky cliffs, dense forests, and picturesque overlooks of the Atlantic Ocean. The trail's name is derived from its narrow ridge-like formation that provides thrilling views on both sides. It's a moderately challenging trail suitable for hikers of various skill levels, and it's an excellent spot for nature enthusiasts, photographers, and anyone seeking a memorable outdoor adventure in Midcoast Maine.

Dolphin Marina & Restaurant

The restaurant at Dolphin Marina sits on the water's edge of Pott's Harbor and offers unrivaled views of Casco Bay and it's many islands. Known for specialties like fish chowder, lobster stew, and blueberry muffins, they also feature Maine lobster dinners, fresh, local seafood, and hand cut steaks.

Cook's Lobster & Ale House

Enjoy a lobster roll on the outdoor deck with panoramic views of the harbor and surrounding islands

Mere Creek Golf Course

Stefan is an avid golfer, so we couldn’t go without throwing a few courses in the mix!

H2Outfitters

Kayak & Paddleboard rentals and tours

Casco Bay Kayak

Kayak tours on the scenic Casco Bay

Wild Oats Bakery & Café

Big Top Delicatessen

Land's End Gift Shop

L.L.Bean

If you happen to stop in Freeport, check out L.L. Bean’s flagship store, which is open 24 hours a day and features a giant Bean Boot out front. Bryce recommends their Wicked Good moccasins for anyone (the best slippers on earth)

Popham Beach State Park

Located near Phippsburg, Popham Beach State Park is known for its long sandy beach, extensive sandbars, and scenic views of the Atlantic Ocean. The beach is part of a diverse coastal ecosystem that includes salt marshes, dunes, and tidal pools, providing a rich habitat for wildlife and a unique environment for exploration. Nature trails wind through the park, offering glimpses of the area's flora and fauna and provide a peaceful setting for walks or birding excursions. Nearby are the remnants of Fort Popham, a historic fortification dating back to the 19th century, adding a touch of historical interest to the coastal landscape.

Portland Head Light

Portland Head Light is a historic lighthouse located in Cape Elizabeth, Maine, known for its picturesque setting and iconic stature. Perched on a rocky headland overlooking the Atlantic Ocean, this beacon has guided ships along the coast since 1791, making it one of the oldest operating lighthouses in the United States. Visitors to Portland Head Light can admire its classic New England architecture, explore the surrounding park with scenic walking trails, and take in breathtaking views of the rugged coastline and open sea.

Old Port

If you’re a foodie, a stop in Portland is a must. Portland’s Old Port is super charming with its cobblestone streets and the city is a hub for restaurants and bars. Whether you're strolling along Commercial Street with views of the harbor, exploring the historic architecture on Exchange Street, or discovering hidden gems in alleyways and courtyards, the Old Port in Portland offers a charming blend of history, culture, and waterfront charm.

Duckfat

The fries are to die for

Blyth & Burrows

Upscale cocktail bar with a speakeasy in the back

Crispy Gai

We ate here the last time we stayed in Portland and the food was incredible. Modern Thai food with incredible fried chicken (get the sauce party if you get the chicken). End your meal with their ice cream sandwich.

Eventide Oyster Co.

Renowned seafood restaurant in Portland

Central Provisions

Local 188

Great for large groups

Allagash Brewing Company

Beer lovers can book a tour or tasting

The Highroller Lobster Co.

Unique lobster rolls in Portland

Portland -Peaks Island Ferry

Once known as the Coney Island of Maine, and later an important WW II outpost, Peaks Island today is a neighborhood within the city of Portland. Home to artists, retirees, commuters of all sorts and a substantial summer population, Peaks Island boasts a small town feel with unparalleled ocean views and access. Fourteen daily departures (17 minutes one way) from Portland make Peaks an ideal, family friendly destination.

Shipyard Brewing Company

The Bait Shed

The cover photo is from this place! Big, yummy lobster rolls with a great view and laid back vibe