35 Best Cocktail Bars near Cumberland

Wander at LongWoods American • $$$
36 Wander Way, 76 Longwoods Road, Cumberland

Customers` Favorites

Pickled Vegetables
Mushroom Risotto
Root Vegetables
Smash Burger
Deviled Eggs
Charcuterie
Lemon Drop
Focaccia
Cobbler
Sorbet

“This place is the definition of real food done right. Everything on the plate is fresh, intentional, and full of flavor-no filler, no fluff. You can actually taste the quality. It’s beautiful, flavorful food that hits differently. The kind of place that makes you want to slow down and enjoy each and every bite.“

4.3 Superb117 Reviews
Central Provisions Tapas/Small Plates • $$$
414 Fore St, Portland - 9.71 miles

Customers` Favorites

Suckling Pig with Marcona Almonds
Selection of Three Cheeses
Caramelized Sheep's Cheese
Bluefin Tuna Crudo Maine
Kombu Cured Fluke Crudo
Confit Local Tuna Salad
Local Oysters Escabeche
Fried Cauliflower Salad
Spicy Raw Beef Salad
Roasted Cauliflower

“Another amazing meal!! We had the kimchi seaweed salad, bluefin tuna crudo, Spanish mackerel, Maine peekytoe crab, fried cauliflower and suckling pig. Everything was so good and it was hard to pick a favorite. I'd have to go with the fried cauliflower. It had such a wonderful spicy and sweet sauce and was cleverly complimented by crunchy fried chickpeas, mint and julienned apple. When you got a bite of everything, the dish practically sang to you. Angie's favorite was the suckling pig. This dish consisted of pork confit which had then been layered into a mold and then topped with crispy pork skin. Then delicately fried again on the flat top grill. It was served with a brown butter apple puree and marcona almonds. It had all the amazing flavors you expect from a great pork roast. No dessert for either of us.“

4.4 Superb298 Reviews
Blyth & Burrows Cocktail Bar • $$
26 Exchange St, Portland - 9.66 miles

Customers` Favorites

Dozen Oysters on the Half Shell
Goat Cheese and Honey
Charcuterie Board
5 Second Frenchie
Mushroom Toast
The Spinacher
Lamb Skewers
Deviled Eggs
Mocktail
Pretzels

“Went for Oyster Social/Happy Hour they do on Wednesdays after a local recommended I try…had a little bit of everything and some punch. I’m not easy to impress. It was DIVINE!!! Delicious fresh seafood, excellent quality, great drinks, just a very nice experience I wish I were local to attend every week! Highly recommend!“

4.7 Superb320 Reviews
Room for Improvement Cocktail Bar • $
41 Wharf St, Portland - 9.73 miles

Customers` Favorites

Soft Pretzel

“Loved the concept. Modern dive bar. Good quality cocktails without the usual stuffiness, and most were only around $13-$14. I usually avoid bars around the Old Port area, but this one seemed different. On a Saturday night, the crowd looked like locals who knew exactly what they were getting.

We walked in at 8 PM to a completely packed house. Handful of booths, bar stools, and some standing tables in the back. We got insanely lucky and swooped into some bar seats the second a group closed out.

The ladies next to us mentioned that Esquire magazine named their Espresso Martini one of the best in the country. Had to try it. They used local Allen’s Coffee Brandy, which gave it a heavier, sweeter, and much more robust punch than a standard vodka-Kahlua build. But it was still the best out of all the martinis we ordered.

The food menu was mostly just dive bar snacks. Cheese balls and hot dogs. They intentionally don’t put much effort into it, and everything was really cheap.

Definitely recommend checking this place out. Just be prepared to elbow into a standing table if you roll in during the weekend rush.“

4.7 Superb137 Reviews
Papi Portland Puerto Rican • $$
18 Exchange St, Portland - 9.67 miles

Customers` Favorites

Arroz Con Gandules Yellow Rice
Street Tacos De Pescado
Ensalada De Zanahoria
Sweet Corn Fritter
Grilled Chicken W
Pork Belly Skewer
Fried Plantains
Crispy Tostones
Crab Alcapurria
Beef Alcapurria

“Just an excellent experience overall“

4.7 Superb259 Reviews
Hunt & Alpine Cocktail Bar • $$
75 Market St, Portland - 9.57 miles

Customers` Favorites

Pimento Cheese & Butter Crackers
House Chips and Dip
Smorgasbord Plate
Swedish Meatballs
Finnish Meatballs
Oysters Rockwell
Danish Hot Dog
Pretzel Pickle
Seafood Board
Deviled Eggs

“Stylish cocktail bar with great drinks and tasty snacks. The cocktails were excellent.
Despite the crowd, the servers were very accommodating and made sure we found a table, which we appreciated.
The popcorn was also delicious, a must-have.
A perfect spot to relax and enjoy a few drinks.“

4.4 Superb117 Reviews
Luna Rooftop Bar Bar • $$
285 Commercial St, Portland - 9.85 miles

Customers` Favorites

Pot Roast Sliders Coconut Fritters Charcuterie Board Burrata and Pot Stickers
Queen of the Coin Alcoholic Beverage
French Onion Dip & Chips
Oysters on the Half Shell
Korean BBQ Beef Sliders
Petite Lobster Rolls
Hummus and Pita
Truffle Fries
Apps at Luna
Purple Haze

“The wife and I had an amazing time for my birthday. Dinner was perfect. Our bartender Mikey was attentive and entertaining. Highly recommend! 5 stars.“

4.7 Superb348 Reviews
The Knotted Apron French • $$$
496 Woodford St, Portland - 9.06 miles

Customers` Favorites

Caramelized Onion and Gruyere Tart
Chicken Liver Mousse
French Onion Tart
French Onion Soup
Chocolate Cake
Cheeseburger
Duck Confit
Profiteroles
Crab Cake
Focaccia

“We absolutely loved our dinner at Knotted Apron. The food was so delicious & inventive but more importantly the service was impeccable and made me feel like I was at home! ❤️ We will absolutely be back soon!“

4.9 Superb120 Reviews
ViA VECCHiA Italian • $$$
10 Dana St, Portland - 9.72 miles

Customers` Favorites

Chocolate Budino
Brussels Sprouts
Sourdough Bread
Whipped Ricotta
Tomato Risotto
Arugula Salad
Seafood Tower
Polenta Fries
Charcuterie
Prosciutto

“Just finished one of the BEST Italian meals ive ever had in my restaurant going life in a place id never have expected to and thats saying something being a 1st Generation Italian coming from NY ! ViA VECCHiA is Portland, Maine was absolutely 10/10 on everything they did! We started with Meatballs, Whipped Ricotta & Grilled Octopus. The meatballs reminded me of my mothers, the ricotta was tremendous with truffle honey & sesame breadsticks and the octopus was grilled perfectly. One dish was better than the next. We shared ravioli with as an entree and we never felt gross like we ate too much. The portion sizes were PERFECT. Wrapped the night off with a espresso infused cheesecake over salted caramel. Wow. Staff was incredibly accommodating, professional and polite. Service was excellent! If youre ever in Portland, ME you must go get a meal here!“

4.4 Superb326 Reviews
Vena's Fizz House Cocktail Bar • $$
90 Bridge Street, Westbrook - 9.87 miles

“Ordered some Nippers off Etsy. Very tasty drinks. Shipping was very Quick and packaging well done. Only thing in would say is the nippers really Don’t make two full drinks unless you add more than the suggested alcoholic or a mixer. We will buy again just the larger sizes.“

5 Superb4 Reviews
The Jewel Box Cocktail Bar • $
644 Congress St, Portland - 9.91 miles

Customers` Favorites

Mocktail of the Month
Leather Belt

“I’ve always had good conversations with the bartenders when I come here! It’s been a bit since I’ve been able to stop by but it’s always on our list when in the Portland area!“

4 Good60 Reviews
Bar of Chocolate Cocktail Bar • $$
38 Wharf St, Portland - 9.74 miles

Customers` Favorites

Chocolate German Cake with Chocolate German Cake Martini
Chocolate Flourless Chocolate Torte
Chocolate Cake with German Frosting
Chocolate Salted Caramel
German Chocolate Cake
Chocolate & Epresso
Dark Chocolate Cake
Vanilla Cheesecake
Key Lime Pie
Creme Brulee

“Best martinis in Portland! It’s a must try if you’re in town. Chocolate salted caramel is my fav 🤤 but, you must ask for Miriam, she’ll take care of you!“

4.2 Good119 Reviews
Rigby Yard Cocktail Bar • $
50 Wharf St, Portland - 9.75 miles

Customers` Favorites

Breakfast Sandwich with Fresh Maine Lobster
Maine Fresh Lobster Roll with Kettle Chips
Lobster Roll & Breakfast Charcuterie
The Cutting Board Charcuterie
Rooster Chicken Sandwich
Depot Garlic Parm Fries
Buffalo Cauliflower
Traditional Fresh
Chicken Wings
Steak Frites

“What a great place to discover!! One of my new favorites! Loved the cool vibe, incredible food, and special cocktails! Can’t wait to go back!!“

4.2 Good144 Reviews
The Continental European • $$
170 Brighton Ave, Portland - 9.32 miles

Customers` Favorites

Crispy Battered Fish and Chips
Golden Fries with Curry Sauce
Shepherd's Pie with Lamb
Grilled Chicken Sandwich
Grilled Strip Steak
Crumpets and Scones
Banger \u0026 Mash
Boxy and Pub Salad
Chicken Schnitzel
English Breakfast

“Fantastic menu! I felt like I just walked into a glamorous pub in England when I saw the menu choices. The cocktail list is loaded with great drinks AND there are two happy hours daily! I had a delicious toasted cheese sandwich with bacon and tomato —so huge I could barely finish half. It came with a heap of perfectly fried hand cut potatoes. My sister got a lovely bowl of French onion soup to start and the steak frites as a main course. There was a big sliced steak done to perfection! We will return regularly! *****“

4.8 Superb188 Reviews
15

Anoche

Anoche Basque • $$
43 Washington Ave, Portland - 9.11 miles

Customers` Favorites

Portuguese Tinned Mackerel 3 Way
Anoche Cheese Board
Goat Cheese & Fig
Charcuterie Board
Meat Board
Seafood

“Warm and comfortable, lovely wine, friendly staff, and tasty food truck offerings.“

4.9 Superb50 Reviews
Salt Yard Cafe & Bar American • $$
285 Commercial St, Portland - 9.85 miles

Customers` Favorites

Salt Yard Breakfast Sandwich
Chorizo and Potato Skillet
Lemon Berry Yogurt Bowl
Cinnamon French Toast
Smoked Salmon Toast
Bacon Egg and Cheese
Sweet Potato Hash
Avocado Toast
Chai Waffle
Lobster Roll

“Looking for a dog-friendly place for lunch and glad we found this place! We weren’t even here two minutes and the servers brought our dog a pup cup and a bowl of water. I usually don’t look for restaurants in hotels when on vacation but this was great! Limited but very good menu.“

4.5 Superb169 Reviews
Bread and Olive Bar • $
935 Congress St, Portland - 9.91 miles

Customers` Favorites

Sourdough Grilled Cheese
Grilled Colossal Shrimp

“Great food made on the premises, including homemade desserts and sourdough bread. Try the charcuterie plate with several cheese, fruit, nuts, bread and a rotating sliced meat. Or the grilled shrimp or tuna, both yummy. Cocktails, wine, espresso -- choices galore. gotta love the espresso martini, even a decaf one! Jazz or blues background music, no headbanger stuff. Relax and enjoy...“

4.9 Superb49 Reviews
Lincolns Bar • $
36 Market St, Portland - 9.65 miles

Customers` Favorites

Rotating Tap

“Great venue, great staff. 10/10 would go every night!“

4.5 Superb112 Reviews
19

REGARDS

REGARDS Seafood
547 Congress St, Portland - 9.74 miles

Customers` Favorites

Hamachi Yellowtail Collar
Caledonia Shrimp Taco
Avacado Salsa Macha
Blue Corn Tlayuda
Grilled Mushrooms
Hiramasa Ceviche
Home-Baked Bread
Scallop Ceviche
Hamachi Collar
Lamb Tartare

“Small menu but very good options of interesting and delicious plates. The avocado crudo, charred cabbage salad and the cod were fantastic. The desserts... Charred corn ice cream and the Peruvian dark chocolate cake - WOW! Nice list of tequilas and interesting cocktails.“

4.2 Good271 Reviews
Boone's Fish House & Oyster Room Seafood • $$$
86 Commercial Street on, Custom House Wharf, Portland - 9.69 miles

Customers` Favorites

Baked Stuffed Lobster 2 Pound Lobster
Boone's Baked Stuffed Lobster
Raw Oysters on the Half Shell
Lobster Mac \u0026 Cheese
Nor' Easter Lobster Roll
Baked Stuffed Haddock
Classic Lobster Roll
Lobster Mac & Cheese
Fish \u0026 Chips
Scallops and Bacon

“Best food I ate in Portland all week (including upscale places) was the lobster bisque from Chef Ryan. Oysters were GREAT as well. Family friendly. Chef Ryan’s whole menu was top notch and the kitchen staff was so nice. Ty came up and offered to give my young kids a lobster lesson over FaceTime (was here for work). Lizzy was excellent at the bar for our group. Ashley was amazing and welcoming to our group. Couldn’t recommend more. But def order the menu items and not just the lobster!“

4.4 Superb335 Reviews
21

ZA

ZA Pizza • $
25 Preble St, Portland - 9.59 miles

Customers` Favorites

Pepperoni Wedge
Pepperoni Pizza

“Went for a lupper date with my husband on the referral of a friend. Had the Natalie house drink which was well balanced and bright for us gin lovers. Enjoyed thier spin on Poutine with a tater tots base. Lots of goo goodness with bacon and sausage. Sausage pizza with Vodka sauce had real Greek olives and was delicious. Will be back again!“

4.7 Superb77 Reviews
The End of Portland Maine Bar • $$
229 Congress St, Portland - 9.23 miles

“Chill intimate environment. Fabulous community. Rotating local art. Fast friendly bar service. Excellent drinks, whether you want a cheap beer or a cocktail. Sober friendly with NA options. Everyone is welcome and treated with kindness. The End is a regular stop for me and I have all the respect for the guys behind it. Check them out! 🤘🏻“

4.8 Superb42 Reviews
Wharf Street Yacht Club Beer Bar • $
43 Wharf St, Portland - 9.74 miles

“pop up with Meet on the Street last night. Prix Fixe four course menu 😋. Food was outstanding, service…outstanding. Drinks?? Always outstanding! The gondola in the bar is always a fun little spot to sit. Such a great space on Wharf St, especially when the snow is falling. Food is warm and lovely, and the staff is always happy to see you. 100/10.“

5 Superb21 Reviews
Three of Strong Spirits Distilleries • $$
35B Diamond St, Portland - 8.97 miles

“A fantastic venue for drinking and dancing. It's a distillery and they craft some fabulous drinks. Rum with salsa dancing is a potent and fun mix. As a senior travel writer and retired professional dancer of 45 years, I did encounter the ageism thing as usual but I am older in comparison to the average person here and expect it. Some were freaked out they had to dance with me in a rotational group. Body language and projection say way more than words. Rather than introduce yourself and give warm welcomes/goodbyes I mostly saw employees/instructors hiding behind their cell phones with slouched postures. That's an avoidance behavior and probably not in the best interests of a growing business. Prejudging a potential customer can cost a business dearly from my experience. But again it's a fine and elegant bar and I highly recommend a visit especially before you dance!“

4.8 Superb35 Reviews
The Garden Café Cafe • $$
20 Milk St, Portland - 9.64 miles

“Top marks for our server who took extra care with our order, separating the soup and salad for sharing. The crab cakes were amazing! We ordered wine which was clearly chosen based on the taste and an easy pairing with menu items. The restaurant sits just outside the hotel allowing guests to enjoy a quiet spot in the city and the lovely outdoors.“

4.6 Superb24 Reviews
26

Inkwell

Inkwell Lounges • $$
119 Exchange St, Portland - 9.52 miles

Customers` Favorites

Lobster Roll

“Todd in the back lounge is the kindest, most talented bartender around. His cocktails are top notch and he is completely dedicated to his guests’ experience. We spend a lot of time at the Press Hotel and have personally witnessed him treating every guest with respect, class and above and beyond service.“

4.5 Superb17 Reviews
UNION Restaurant New American • $$
390 Congress St, Portland - 9.51 miles

Customers` Favorites

Deconstructed Cheesecake
Salad of Autumn Greens
Lobster Eggs Benedict
Classic French Toast
Standard
Burger
Salad
Roll

“Enjoyed breakfast here:
- 2 coffees
- Eggs and corned beef hash
- Eggs and bacon

While the service, quality, and quantity were top-notch, our total - after gratutity - was $73.00. Sorry, but that is a ridiculous amout for breakfast for 2 adults.

Aside from the toast being drechned in butter, the food was well-prepared and delicious. The coffee was fresh and super hot, and our waitress ensured our coffee - and waters - were always full.“

4.1 Good151 Reviews
Tipo Restaurant Italian • $$
182 Ocean Ave, Portland - 8.3 miles

Customers` Favorites

Spaghetti and Meatballs
Margherita Pizza Brunch
Fennel Sausage Pizza
Tipo Pepperoni Pizza
Local Greens Salad
Rigatoni Carbonara
New Yorker Pizza
Cauliflower Dip
Pizza Margherita
Beef Carpaccio

“Great service, lovely atmosphere and the food was delicious. Pizza was the star of the show, but the rye cavatelli was a nice, bright dish.

Pasta serving was too small for the rather high price, but supporting quality neighborhood places like this outweighs the slight wincing at the final bill.“

4.3 Superb110 Reviews
Grace Wedding Venue & Event Center American
15 Chestnut St, Portland - 9.48 miles

“We had our wedding at Grace and it was such an amazing event. Meg was incredible, she went above and beyond to make sure that we had everything that we needed and that we had a very smooth celebration on the day of. The space was immaculate without having to do a ton of extra work. The venue was also in a great location and easy for folks to get to. Would highly recommend this beautiful venue and Meg is such a boss!“

4.6 Superb15 Reviews
Five of Clubs Bar • $$
754 Congress St, Portland - 9.94 miles

“Very nice layout that’s small but big enough for those staying in the area. Not super busy in evening or morning. Vintage yet updated modern clean feel throughout. Nice cafe next door support great breakfast and coffee and utilizes this space in the Longfellow lobby for seating. Great vibes, low to moderate noise that you can still hear a normal conversation.“

4.4 Superb14 Reviews
The Independent Ice Co. Bar • $$
52 Wharf St, Portland - 9.75 miles

Customers` Favorites

Southern Fried Chicken Sandwich
Daily Cocktail Special
Templeton Rye 10 Year
Buffalo Cauliflower
Philly Cheese Steak
Independent Burger
Maine Lobster Roll
Charcuterie Board
The Cutting Board
Cheese Tortellini

“This might be the best overall bourbon list I have ever seen at an establishment. Prices were reasonable as well. I just wished they opened earlier than 4pm. Burger next door at Rigby is 5 stars.“

4.4 Superb129 Reviews
32

Lenora

Lenora Mexican • $$
2 Portland Sq Ste 100, Portland - 9.71 miles

Customers` Favorites

Oaxacan Hot Chicken Sandwich
Eggplant Milanesa
Seafood Tostadita
Chile Con Queso
Carnitas Tacos
Breakfast Taco
Baja Fish Taco
Tijuana Caesar
Migas Burrito
Chicken Tinga

“An absolute gem in the heart of the old port. The margaritas are the best in all of Portland and served by the friendliest / warmest locals around. Not enough space to talk about the divine cuisine. ¡Salud!“

4.2 Good199 Reviews
Off Track Pizza Pizza Takeaway • $
15 Exchange St, Portland - 9.65 miles

Customers` Favorites

Truffle Mushroom Sausage
Cheese Pizza to-Go
Sausage & Pepper
Pepperoni Pizza
Pepperoni Slice
The Mootz Slice
Vodka Burrata

“Fire pizza service everything about this place is awesome if you haven’t tried not tried it your losing out amazing food get some“

4.3 Superb113 Reviews
Black Cow Burgers & Fries Hamburger • $$
83 Exchange St, Portland - 9.56 miles

Customers` Favorites

Burger Chicken Sandwich and French Fries
Sour Cream and Onion Fries
Cheeseburgers and Fries
Mushroom Swiss Burger
Cheeseburger Sandwich
Fried Brussel Sprouts
Fried Brusselsprouts
Slushie Burger
Cheese Burger
Regular Fries

“Visited Saturday night. Delicious food at good prices. Great service. Relaxed atmosphere.“

4.2 Good188 Reviews
Harbor Bistro + Terrace Seafood • $$$
468 Fore St, Portland - 9.76 miles

“What an amazing experience. We would definitely recommend and will be back soon!“

3.2 Average37 Reviews