Start from 81 curated places around Portland, ME, then choose the recommendations that fit your guests.
Restaurants & cafés
Eventide Oyster Co.
An oyster bar near the foot of Munjoy Hill with a couple dozen East and West Coast varieties on crushed ice and a James Beard Best Chef nod behind it. The brown-butter lobster roll on a steamed Chinese-style bun is the order people travel for. Counter-and-stool setup, no reservations, expect a wait.
Fore Street
A wood-fired Old Port institution open since 1996, cooking everything over an open hearth and turnspit with ingredients from Maine farms and boats. The applewood-roasted mussels and the nightly spit-roasted pork are longtime anchors. Dressy-casual, special-occasion energy.
Trails & outdoors
Eastern Promenade Trail
A flat, fully paved roughly 2-mile waterfront path along Casco Bay below Munjoy Hill, passing marinas, East End Beach, and the narrow-gauge tracks. Open to walkers, runners, cyclists, and strollers. The easiest scenic walk in the city.
Back Cove Trail
A flat 3.5-mile crushed-stone and paved loop around the Back Cove tidal basin with open skyline views of the Portland peninsula. Popular with runners and dog walkers in every season. Easy, exposed, and great at sunset.
Things to do
Portland Museum of Art
Maine's largest art museum, downtown in the Arts District, with a strong Winslow Homer collection plus American and European holdings and rotating shows. The Homer galleries and the architecture-spanning campus are the core. The anchor indoor cultural stop.
Casco Bay Lines
A working mailboat ferry through several Casco Bay islands on the country's oldest continuously running ferry service. You ride alongside residents and freight on a real route, not a tour boat. The most authentic and affordable way to see the bay.
Landmarks & sights
Portland Head Light
Maine's oldest lighthouse, commissioned in the 1790s, set on the rocky headland of Fort Williams Park in Cape Elizabeth. The light tower itself is closed but the keeper's house museum and the surrounding cliffs and lawns are the experience. The single most photographed spot in the region.
Portland Observatory
An 1807 wooden maritime signal tower on Munjoy Hill, the last of its kind in the country, once used to signal ship owners about incoming vessels. Climb the interior stairs for a guided 360-degree view over the harbor and islands. Open seasonally with timed tours.