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May 24, 2025
Scarborough, ME

Alexander & Kasey

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    Places to Eat & Drink

Places to Eat & Drink

When we were dating in college, we loved going into Portland to celebrate special occasions. Over three years, we explored many of Portland's amazing restaurants. The ones listed below are a collection of some of these dates and have a special place in our hearts. If you're looking for something to do over the long weekend, these are our best recommendations - we especially recommend exploring the Old Port neighborhood and all of its shops & restaurants.

Restaurants

Via Vecchia

10 Dana Street, Portland, ME 04101

Great Italian food in a cool, Old Port building. We went here for Valentine's Day in 2022.

Central Provisions

414 Fore Street, Portland, ME 04101

Small plates and snacks. Great for pre-dinner cocktails and appetizers.

Union Restaurant

390 Congress Street, Portland, ME 04103

Delicious food inside the Portland Press Herald hotel. We went here for our one-year anniversary.

Chaval

58 Pine Street, Portland, ME 04102

Cute neighborhood-style restaurant with Spanish and French cuisine. We went here for Valentine's Day in 2021.

Little Tap House

106 High Street, Portland, ME 04101

Casual American cuisine. We went here before seeing the band Caamp at State Theatre in December 2021.

David's Restaurant

22 Monument Square, Portland, ME 04101

Restaurant owned by popular Maine chef, David Turin. We went here for Valentine's Day in 2020.

Tuscan Table

390 Gorham Road, South Portland, ME 04106

Homemade pasta and other Italian cuisine. We went here for our two-year anniversary.

Becky's Diner

390 Commercial Street, Portland, ME 04101

Classic diner food and a staple for Mainers. Kasey worked here in college, and her mom still works here!

The East Ender

47 Middle Street, Portland, ME 04101

Fun, unique cocktails and cuisine. We went here for a date night in 2021.

Boone's Fish House & Oyster Room

Custom House Wharf, Portland, ME 04101

Classic Maine seafood. We went here for Kasey's 21st birthday lunch.

Bars

Rí Rá Irish Pub & Restaurant

72 Commercial Street, Portland, ME 04101

Irish pub - speaks for itself.

Lincolns

36 Market Street, Portland, ME 04101

Fun speakeasy downtown. Good luck finding the entrance.

Three Dollar Deweys

241 Commercial Street, Portland, ME 04101

Casual pub. $3 drinks (supposedly)

Maine Beer Company

525 U.S. 1, Freeport, ME 04032

The best beer in Maine, according to Alex. Try a Lunch beer!

Flight Deck Brewing

11 Atlantic Avenue, Brunswick, ME 04011

If you're up for a drive, this was our favorite hangout spot near Bowdoin. Located on former Naval Air Station Brunswick, they have great beers and pizza. Go check out Bowdoin while you're there!

Sea Dog Brewing Company Topsham

1 Bowdoin Mill Island, Topsham, ME 04086

Another go to hangout spot near Bowdoin's campus. Blueberry beers are the only option.

For all the days along the way
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