Outdoor Dining in Portland

The arrival of tables and chairs on Portland’s sidewalks is one of the surest signs that summer is on it’s way

Isa Bistro | 79 Portland St.
This unassuming neighborhood favorite has a tucked-away patio, hidden from view by a wooden fence. “Twinkly lights strung over a cozy, intimate alleyway. Straight magic,” says advertising account manager Jessica Goodwin. “Makes you feel like you’ve been transported to some far-off European place.”

David’s | 22 Monument Sq.
With a diverse menu and well-prepared dishes, David’s is an easy choice for any mood. But on a sunny, summer afternoon, happy hour at one the restaurant’s outside tables in Monument Square feels like more of a must than an option.

Dimillo’s on the Water | 25 Long Wharf
Dimillo’s is the only restaurant in Portland that can claim to actually be on the water. The floating restaurant features multiple decks and a lengthy history along the waterfront. Tony DiMillo moved his restaurant to Commercial Street from Fore Street in 1965, before opening on the former car ferry in 1982

Portland Regency Hotel’s Garden Cafe | 20 Milk Street
This outdoor eatery is located across from the hotel’s brick-lined entrance on Milk Street. Open for lunch and dinner, the cafe feels secluded despite being in the Old Port. The bistro tables and chairs along the arced lawn are ideal for a relaxing meal or drinks with friends.

Diamond’s Edge Restaurant & Marina | 1 Daimond Ave., Great Diamond Island
Located on Great Diamond Island, a short ferry ride from the Old Port, this seasonal restaurant offers outdoor seating on a spacious deck and its lawn along the water. There’s seating inside, but that doesn’t share the same unobstructed views of Diamond Cove.

Portland Lobster Company | 180 Commercial St.
Classic seafood shack fare, live music, local beer, and, of course, plenty of lobster make this seasonal eatery popular for both tourists and locals. With an expansive patio that extends out on a pier, diners get to experience all the sights (and salty smell) of Portland’s waterfront.

Slab | 25 Preble Street
Famous for its namesake pizzas—pillowy dough topped with a sweet tomato sauce and cheese—Slab becomes an outdoor eating mecca in the summer. The downtown restaurant features large, communal picnic tables, a well-curated tap list, and a thoughtful menu that reaches beyond the Sicilian-style pizza

Novare Res Bier Cafe |  4 Canal Plaza
Firmly established as a beer destination, Novare Res also features unique, internationally inspired food options, from German sausages to the crab rangoon grilled cheese. Along with the best tap and bottle list in Portland, this bar has a secluded downtown patio sandwiched between a few buildings.

The Port Hole |  20 Custom House Wharf
Boasting a lengthy deck along Custom House Wharf, the restaurant has been a fixture on the waterfront for years. “To me, nothing beats a lazy summer Sunday afternoon at the Porthole,” says Chris Kast, brand director at Brand Co. “It makes me feel connected to the city and our working waterfront heritage.”

Sonny’s | 83 Exchange St.
The opposite of secluded, Sonny’s outdoor seating is in the middle of the Old Port, looking out on the bustling Post Office Park. A favorite for post-work drinks, the central location makes for prime people watching.



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