Rooftop Bars + Waterfront Eats in Greater Portland

Rooftop Bars + Waterfront Eats in Greater Portland

Get a Taste of the High Life in Maine

Sip, Savor, and Soak in the Views

High above the bustling streets and nestled along the Portland’s working waterfront, you’ll find rooftop bars + outdoor eats that provide an elevated experience like no other. But where should you go for the finest culinary and beverage adventures? Keep reading to explore exceptional venues that promise a memorable visit any time of the year.


Top of the East at the Westin

If you’re a first-time visitor and a fan of rooftop bars, you can’t miss a visit to Top of the East. Situated on the top floor of the Westin Portland Harborview , this rooftop gem has recently undergone a fantastic renovation. You’ll find luxurious seating and breathtaking scenes that showcase a panoramic view of Portland. With a full bar and bites menu, you’re sure to find exactly what you’re craving while on vacay. The best part about this venue being indoors with floor-to-ceiling windows is you get the rooftop bar experience rain, snow, or shine.

Luna Rooftop Bar at the Canopy Portland Waterfront

Hot, summer nights are no match for the ambiance and atmosphere you’ll find waiting for you at Canopy Portland Waterfront‘s Luna Rooftop Bar. Try crafted cocktails like Persephone, a bright, effervescent cocktail made with Citrus Vodka, Cappelletti Aperitivo, Prosecco, and Lemon. Don’t forget about the bites, like the Seafood Tower. It is perfectly portioned for 2-4 people and features lobster tails, oysters, poached shrimp, and salmon poke. Combine that with its stunning view of the Old Port and Casco Bay, and you’ll quickly realize why it’s a favorite with locals and out-of-towners.

Bayside Bowl

Yes, Bayside Bowl is technically a bowling alley, but come up to the roof and you’ll find one of the most chill spots in town. Locals love it for happy hour. Don’t forget to bring your appetite because you’ll find tacos, rice and bean bowls, quesadillas, and more from their Airstream trailer. They also have a rotating menu of frozen drinks in the warmer months and host movie nights on the roof.


DiMillo’s on the Water

The only thing better than dining on a boat is drinking cocktails on a boat on a rooftop deck! DiMillo’s is a Portland institution for many reasons, including having one of the best ocean views in the Old Port. You can experience that view on one of their incredible decks when you’re outside on a hot, sunny day. It’s the perfect spot to grab a quick nibble, like their crab cakes, fried oysters, or jumbo shrimp.

Besides the food, and obviously, the seafood, another place that DiMillo’s truly shines is the drinks. Enjoy a beverage on the deck, like their immensely refreshing Summer Solstice cocktail. Made with sparkling wine, limoncello, raspberry puree, and topped off with ice, you’ll feel like you’re on vacation the second you take the first sip and look out at the spectacular harbor views.

Ri Ra Irish Pub & Restaurant

Get the rooftop views you’re craving while staying inside by checking out Ri Ra Irish Pub & Restaurant! Located about as centrally as it gets in the Old Port, Ri Ra has views, craft beer, and the Irish food you’ve been craving. Who said you have to sit on a roof to get rooftop views? This is not the case when you stop in Ri Ra. One of the things that people love most about this established eatery is there’s almost always live music being played.

Whether it’s a traditional Irish band or a cover band that makes you tap your feet, you can’t help but have a fantastic time here. Guinness flows plentifully on draft here, along with a Rotating Slushee, a Hibiscus Mexican Mule, or the RBL, made with Red Bull Blueberry, Absolut, lemon, and simple syrup when you need a little extra kick to keep you going!

Luke’s Lobster Portland Pier

It’s hard not to find something to like at Luke’s Lobster Portland Pier. Like lobster rolls? You’ll find plenty of creative varieties of lobster rolls here! Looking for waterfront views to enjoy while you eat and drink? Luke’s Lobster boasts one of the most beautiful decks downtown. The double-decker deck is stunning inside and outdoors, but sitting outside on a balmy summer evening is a must.

There’s no better spot in town than this rooftop spot to start with some steamers, followed by a Maine Mule, consisting of local vodka, fresh lime, and a little Maine Root Spicy Ginger Brew. It’s a Maine twist on a summer classic for the nights that you never want to end.

Flatbread Company

Have you seen the views at Flatbread Co? The perfect place to consider for outdoor and waterfront eats in Portland. After all, the central location, great pizza, and panoramic views can’t be beat. If you like your pizzas crispy and bursting with fresh, local ingredients, you’ll find what you’re looking for at Flatbread.

Grab a seat on their gorgeous outdoor deck and order a root beer float or a Peace of Mind Whoopie Pie to split if your sweet tooth wants a little attention. It’s hard to say no to the Rhubarb 75 when you want a cocktail after work, made with Sweetgrass Distilling Rhubarb Smash liquor, Jugger and Jones gin, lemon juice, simple syrup, and topped with Prosecco. No matter what you’re in the mood for, you’re sure to find something that suits the occasion on Flatbread’s incredible outdoor deck.

Get Your Foodie Fill

Trio of Lobster Rolls on Peaks Island, Photo Courtesy of Kirsten Alana / GLP Films

Want more seaside eats? Find restaurants tucked away on historic cobblestone streets or scattered across our sandy beaches.