New England’s Coziest Winter Weekend Getaways

The darkness of winter mornings always reminds me of one thing: it’s too cold to get out of bed. Alas, I stumble out of bed wearing a sweater like a hug from an old friend, into the kitchen where I hear the tea kettle about to whistle. I see Jack Frost and his friends painted on the windows overnight as I shrug off the chill of wondering why it doesn’t feel like the heat is on. As I slip into my L.L. Bean moccasins, I sit down at my desk. Hmm, I wonder. Where is the coziest place I could be right now?

So you didn’t get that tropical vacation for Christmas this year? It’s totally cool – I didn’t either. Every year, like clock work, the day after Christmas my favorite retailers go straight for the resort collection. I’m a little perplexed – does everyone else get to skip winter? Last time I checked – the groundhog never sees his shadow and there are always 6 more weeks of winter. Alas, I guess that’s a rant for another day.

My mind doesn’t go very far. Some of the most cozy winter inn and getaways are only a short car ride away. While it is always exciting to get on a plane, I love being able to get home in just a few short hours, sans jet lag. If you could guess – my favorite places to grab a long, slow cup of coffee are here in the New England winter tundra.

Stowe, VT

I have been going to Stowe, VT since I was in high school. From the 100s of km of nordic trials to Mt Mansfield herself, you will have no shortage of winter fun. Sledding, horse drawn carriages, and ice skating are also appreciated winter sports. More into apres ski? This area is lined with delicious breweries, like the Alchemist and Lawson’s Finest (~ 20 miles south). There are also boutique shopping areas and cozy cafes. After a day of skiing or relaxing, there is boutique shopping and cozy bars to watch the game

Bennington, VT

Nestled in the mountains just east of upstate New York, this Vermont town is rich in culture. A haven for artisans and students alike, this tiny town boasts homemade treasures, like the mugs from Bennington Pottery (we have quite a few). Make sure to swing by the Bennington museum for a dose of New England folk art by Grandma Moses and learn about the battle of the Bennington. You can usually snag tickets from your lodging – we got ours from Lynn the owner of the Four Chimney Inn. Planning a trip for March? Enjoy the sweetest weekend of the year, when all the sugar shacks open for the season in an event called Maple Sugar Weekend. I’m giving away a TWO NIGHT stay at the four chimney inn on my instagram: check it out here

For the full run down, see my guide on Bennington, VT

Freeport, ME

Tucked in to coastal southern Maine is a the treasured town of Freeport. A great mid point for all of what coastal Maine has to offer. Famously known for its 24 hour L.L. Bean headquarters, Freeport is known for its shopping. In the surrounding areas you will find state parks with snowshoeing & xc ski tracks or just take a drive up to Portland for the day and enjoy a day of shopping and gluttony. Make sure to pack your bean boots – guide on choosing the right fit is in my Freeport guide below.

For the full run down see my guide on Freeport, ME

Jackson, NH & Franconia Notch 

Jackson, NH and Franconia Notch are famously known for their grandeur. Take a ride on the slopes on one of the many regional mountains and make sure to snag a good luck kiss on this covered bridge. I can also attest that their xc ski trails are sublime (snow shoe rental also available). We recommend staying in one of the historic inns in North Conway or Jackson. A tiny neighboring villages right off the highway, one of these towns (North Conway) is home to a candy store fit for any elementary schoolers dream along with great places to grab lunch. On the way home be sure to snap a picture of the grand Washington hotel, or grab a heaping plate of pancakes in the parlor.

Bethel, ME

A mountain retreat known best for it’s proximity to Sunday River, this ski town has more to offer than lift tickets (although we definitely suggest grabbing some). During the winter season, you’ll find the some of the finest alpine skiing in the east, snowmobile rentals/trails, and zip line tours pop on your snowshoes and explore the White Mountain National Forest.