Spend a Winter Weekend in Portland, Maine

Advisor - Sarah Roof
Curated By

Sarah Roof

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  • Portland, Maine

  • Boutique Travel

  • City Travel

  • Outdoors

  • Sightseeing

  • Entertainment

  • Local Culture

Wine of Portland
Curator’s statement

Renowned for its vibrant coastal charm and picturesque landscapes, Portland, Maine holds a special allure, particularly during the winter season. While the city may be traditionally adored for its bustling summer activities, winters in Portland unveil a different kind of enchantment. As snow blankets the city, the quaint streets transform into a serene winter wonderland, exuding a quiet and magical ambiance. The historic Old Port district, adorned with twinkling lights and inviting boutique windows, offers a cozy respite for visitors seeking warmth and comfort in the heart of the snowy season. From savoring freshly caught seafood and expertly crafted cocktails in cozy, fireside restaurants to exploring the snow-covered trails of the nearby Portland Head Light, every winter moment in Portland exudes a unique sense of tranquility and beauty that solidifies its position as a captivating year-round destination in the heart of Maine.

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Where to stay in Portland, Maine

The Press Hotel, Autograph Collection

In the heart of Portland, Maine, this historic hotel features a fun newspaper-theme with rooms and suites styled as writer's offices.

Fora Perks
  • $100 hotel / resort credit.

  • Welcome amenity.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

The Westin Portland Harborview

It’s all about the views at this renovated Portland landmark between Old Port and the West End, now home to a must-visit rooftop bar on the 15th floor.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Blind Tiger Portland – Danforth Street

Savor inventive cocktails and delectable cuisine at Blind Tiger on Danforth Street, where hidden delights await.

Advisor - Sarah Roof

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Things to do in Portland, Maine

A variety of boats leisurely sailing along the coast of Portland Maine, with Peaks Island faintly visible in the background.

Mailboat Tour

The Mail Boat Tour in Portland, Maine offers a uniquely enchanting (and affordable!) opportunity to witness the rugged coastal beauty and serene winter landscape. It provides an intimate glimpse into the local community's way of life and the breathtaking charm of the region, even amidst the colder months. If you're lucky, like we were, a friendly local may even invite you to check out their home on one of Maine's various secluded islands during one of the extended stops!

Self-Guided Brewery Tour

With over 25 breweries in the Portland area, this is your chance to explore the local craft beer scene! Mix and match well-known favorites like Allagash and Shipyard amongst local gems like Austin Street, Bissel Brothers and Rising Tide for the ultimate beer expedition.

Winter Lighthouse Tour

Experience the ethereal beauty of snow-covered lighthouses such as the iconic Portland Head Light and Spring Point Ledge Light.

Ice Skating in Deering Oaks Park

Glide across the frozen surface of Deering Oaks Park's ice skating rink, surrounded by the peaceful wintry landscape and reflections of twinkling lights. This is a delightful and festive outdoor activity for families and friends alike that is surely not to be missed!

Explore the Portland Museum of Art

Cold weather not really your thing? Immerse yourself in the captivating world of art and culture showcased at the Portland Museum of Art. Here you can admire a diverse collection of works, including contemporary and classic masterpieces, providing a warm and enriching cultural experience amid the winter chill.

Shopping in Old Port

Amble down the charming cobblestone streets to find an incredible selection of boutique shops and local artisanal stores. Old Port provides the perfect cozy and inviting atmosphere for finding unique gifts and treasures like jewelry, leather goods, locally-crafted art, and more!

Explore the West End

Home to the Victoria Mansion and a collection of other historic homes, the West End captivates with its timeless charm and vibrant community, offering a blend of Victorian-era architecture, tree-lined streets, and an eclectic mix of locally-owned shops, cozy cafes, and inviting restaurants.

Lunch on some lobster

Did you even really go to Maine if you didn't try some lobster? Get some of the freshest seafood you will ever have at one (or two, or three...) of the city's favorite spots!

Places to eat & drink in Portland, Maine

meat and chips


The Holy Donut: Potatoes? In donuts? They make it work! Check out their delectable daily selection of fresh-made potato cake donuts for something new, sweet, and exciting.

The Friendly Toast

Who doesn't love a kitschy diner with an eclectic menu for brunch? Churro bites, breakfast egg rolls, cookie monster pancakes, mimosa flights, and more make choosing what to order a tough job!


Eventide Oyster Co.

Indulge in the most unique (and iconic) lobster roll in the city! Known for their Brown Butter Lobster Rolls, Eventide's innovative seafood dishes put the perfect spin on Maine's coastal flavors and culinary excellence.


Did someone say comfort food? The best spot to cozy up with some gourmet duck-fat fries (with a flight of dipping sauces!) and a milkshake is in Duckfat's snug eatery.

Luke's Lobster Portland Pier

You can never have too much lobster in Portland, and with 360-degree views of the gorgeous Portland waterfront, what better way to let your tastebuds decide who has the best lobster rolls in the city?

Bite Into Maine

Ok... just one more! Even though some lobster shacks take a winter break in January, you can check out Bite Into Maine's food truck serving up lobster roll FLIGHTS at Allagash Brewing Company! Two birds--three lobster rolls--one stone.


Blyth and Burrows

This sophisticated and romantic cocktail bar offers a curated wine list and expertly crafted cocktails with a nautical spin. My personal faves were the 5-Second Frenchie and the Jewel of the East, featuring a diamond-shaped ice cube.

The Jewel Box

With a speakeasy vibe and attentive service, the Jewel Box wows with their moody atmosphere and creative cocktails. This is a quirky spot that will surely offer a unique cocktail-sipping experience.

Advisor - Sarah Roof

Travel Advisor

Sarah Roof

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