5 Places to Eat and Drink During the Off-Season in Portland, Maine

Words by Katherine Oakes
Photos by Katherine Oakes

A love of good food and drinks is reason enough to make you travel around the world and it’s certainly one of the best excuses for visiting Portland, Maine in the dead of winter. This New England hub is known for its eateries, as Bon Appetit pointed out when they named it the “Restaurant City of the Year” in 2018. But why wait for a table at one of the hottest places in town during the hottest time of the year when you can make the most of the off-season and eat your way through Portland?

Don’t let the frigid temps scare you off, the secret to making the most out of this snowy city by the sea involves a (really) good local beer, plates of food and some good company gathered around the table.

Here are 5 places to eat and drink during the off-season in Portland, Maine.

Tomaso’s Canteen

At first glance, Tomaso’s looks like an unassuming local watering hole. Behind its somewhat divey appearance is a popular hangout with good music, great booze and delicious eats. Tomaso’s is the kind of spot with an understated cool yet friendly atmosphere that makes you feel like you’ve been coming here for ages. It’s the ideal spot to hunker down on a cold winter evening, whether you’re just beginning or ending your night.


A punch of warm, Southern BBQ and Southwestern fare in the middle of the winter is exactly what you need to perk up. Bright and colorful décor, with a fun and upbeat vibe that is distinctly different from your classic New England eatery, Terlingua excels in mouth-watering plates with a little extra kick. Their menu falls more in line with the tiny but mighty variety, so try not to over order —you will be surprisingly full. Some favorites are the enchilada suizas, small batch smoked meats and a hearty serving of crispy jalapeno cornbread.


There are some nights when you want a spot that’s hip without being highbrow and a tasty menu that one could call, “elevated pub food” — in a good way. The West End’s LFK is your go-to for all of that. It’s got a relaxed and eclectic vibe so you can sip on cocktails and famous Maine craft brews or let your snacking turn into a full meal with friends. And if you’re staying in town, it’s an easy stumble home on a late, snowy night.


Hand cut Belgian fries and signature poutine fried in duck fat have made this restaurant one of the most popular places to eat in Portland. The winter is primetime for out-of-towners looking to try their famous comfort food for two reasons: First, you won’t have as long of a wait as you would during the summer and second, well, this type of cuisine was made for warming up when the mercury drops, right? So, pull up a chair and prepare to dig in.

Empire Chinese Kitchen

There’s something so indulgent about crowding around a table full of steamed dumplings, ginger-fried rice and warm sake during the dead of winter that makes Portland’s Empire Chinese Kitchen worthy of this list. This Chinese eatery is warm, cozy and bright with hot plates that will continue to conjure mouth-watering memories long after you’re done. Meals here feel intimate and fun, which is the perfect vibe for a night of seemingly endless amount of shared Chinese plates with friends.

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