Hey! 👋 I'm your WKND Concierge, your personal AI travel companion.
Ask me anything about weekend trips, restaurants, hotels, or experiences. I can also help you plan right now!
What are you looking for today?
Weekend Trip from Boston to Portland, Maine — Relaxing Foodie Itinerary | WeekendTrips
Weekend in
Portland
0 Gem ScoreApr 28from BostonFriends
Day One ·
Morning
Eventide Oyster Co.
Arrive by 6 p.m. and check into your accommodation. Head directly to Eventide Oyster Co. (86 Middle Street) for dinner—their wood-roasted oysters and brown butter lobster roll are reasons enough, but the candlelit, convivial dining room sets the tone for the weekend. Arrive by 7 p.m. to avoid a wait, or grab seats at the bar.
Day Two ·
Morning
Portland Roasting Company
Start at Portland Roasting Company (111 Commercial Street) with excellent single-origin coffee while watching fishing boats work the harbor. Grab pastries and sit on the waterfront bench—this is the local ritual, unhurried and free.
Afternoon
Portland Museum of Art
Spend 2–3 hours exploring Portland Museum of Art (7 Congress Square)—their Maine galleries and contemporary wing are world-class without the crowds of Boston MFA. Afterward, drift through the Old Port's independent bookstores (Longfellow Books) and vintage shops on Congress Street.
Evening
Hugo
Dinner at Hugo (60 State Street)—intimate, chef-driven New England fare with impeccable seafood, the kind of place where the chef actually greets you. After, grab a nightcap at Blyth & Burks (47 Middle Street), a wine bar disguised as a flower shop with natural wines and a genuinely quirky Portland vibe.
Day Three ·
Morning
The Good Table
Brunch at The Good Table (527 Congress Street)—inventive small plates, killer Bloody Marys, and zero pretension. Then walk off breakfast by exploring the Eastern Promenade Trail, a 2-mile waterfront path with views of Casco Bay and genuine local joggers, not selfie-takers.
Departure
Departure
Leave by 2 p.m. to beat traffic. Return via I-95 South—the drive is straightforward and takes 1 hour 45 minutes. No scenic detours needed; the return itself is meditative.
🔒
2 more days planned for you
Sign up free to see the rest of this itinerary, save it, and generate your own for any city.
