Portland · Weekend itinerary
A Weekend in Portland, Maine for Grown-Ups
Two days is the classic Portland weekend: the Old Port and the bay on Saturday, the lighthouses on Sunday, and two very good dinners.
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Day 1: The Old Port and the bay
Oysters, islands and a wood-fired dinner.
Lunch
Eventide Oyster Co.
86 Middle St, Old Port
Oysters and the brown butter lobster roll.
A James Beard Award-winning raw bar with fresh oysters and shellfish and the famous brown butter lobster roll. Indoor and outdoor seating.
Afternoon
Casco Bay Lines Mailboat Run
Ferry terminal, 56 Commercial St
The noon or 3:15 p.m. mailboat among the islands.
Ride along on the working ferry that delivers mail and freight to five Casco Bay islands, including Great Diamond, Long and Chebeague. Two and a half to three and a half hours, year-round, departing 10 a.m., noon and 3:15 p.m.
Sunset
Top of the East
Westin Portland Harborview, 157 High St, 15th floor
A drink fifteen floors up.
A 15th-floor lounge with views over the city to Casco Bay, cocktails and small plates. Opens at 4 p.m. daily, until midnight on Fridays and Saturdays; reservations on OpenTable.
Dinner
Fore Street
288 Fore St
Book ahead by phone.
Portland's landmark since 1996: a big old warehouse room around a wood-fired oven, grill and turnspit, with a menu that changes daily with what farmers and fishermen bring in. Open nightly from 4:30 p.m.; reservations by phone.
Late
Hunt + Alpine Club
75 Market St
Cocktails on Market Street (closed Mondays).
A two-time James Beard semi-finalist cocktail bar, opened in 2013 and renovated in 2025, with food to match the drinks. Opens at 3 p.m. Tuesday to Friday and 2 p.m. at weekends; closed Mondays. A few reservations are released, the rest is walk-in.
Day 2: Lighthouses and a waterfront dinner
Cape Elizabeth by day, back to the waterfront at night.
Morning
Portland Head Light & Fort Williams Park
1000 Shore Rd, Cape Elizabeth (15 minutes)
Heads-up: The lighthouse museum closes for the season after Indigenous Peoples Day (October 12, 2026).
Go early, before the parking fills up.
The classic Maine lighthouse, on the rocks inside a free public park with old gun batteries, the Goddard Mansion ruin and a small cove beach. The park is open sunrise to sunset year-round; parking is by card meter.
Lunch
The Lobster Shack at Two Lights
225 Two Lights Rd, Cape Elizabeth
Heads-up: Seasonal: the 2026 season ends October 25.
Lobster by the sea (seasonal).
A lobster shack on the rocks by the sea, a local landmark since the 1920s, with picnic tables facing the ocean and the Two Lights lighthouse. Open daily 11 a.m. to 8 p.m. in the fall.
Afternoon
Portland Observatory
138 Congress St, Munjoy Hill
Heads-up: Seasonal: open daily 10 a.m. to 3:30 p.m. until October 12, 2026, then closed for the winter.
Climb the 1807 signal tower (until October 12, 2026).
An 1807 maritime signal tower on Munjoy Hill, with 45-minute guided climbs to a 360-degree view of the harbour and islands.
Dinner
Street & Co.
33 Wharf St
Seafood on a cobblestone lane.
A seafood restaurant on a pedestrian cobblestone lane between Commercial and Fore streets. Dinner nightly from 5 p.m.; a few walk-in tables are held each evening, with sign-ups from 4:30 p.m.
Staying longer? Our 3-day Portland itinerary adds a food tour, Twelve and a day on the coast at Ogunquit.
Everything here was checked in September 2026. Many places on the Maine coast are seasonal and close or cut their hours from mid-October, so confirm before you go.
Questions people ask
Is a weekend enough for Portland, Maine?
Yes, for the Old Port, a boat trip and Portland Head Light. Add a day for the coast or a spa afternoon.
What should you not miss in Portland, Maine?
Oysters at Eventide, dinner at Fore Street, a boat on Casco Bay and Portland Head Light.