Southern Vermont Winter Travel Guide
We have a soft spot in our hearts for Vermont. In particular, Southern Vermont. Because that little corner of the state happens to be our home away from home. A few years back we bought a little place in the mountains not realizing how much it would give back to us. We thought it would be a good property investment, but what we didn’t realize is that we were really investing in ourselves. Because Vermont truly fills us up. After hectic weeks at work, a drive down the country roads to our little piece of heaven is therapeutic beyond words. We never knew we would grow to love this place so much.
Our little spot is on Stratton Mountain, just around the bend from the charming town of Manchester and a stones throw away from so many other adorable spots in the region. And although we initially thought skiing would be our main draw to the area, we quickly realized it offers so much more. Every season seems to serve up something special in Vermont, but as a certified summer lover, winter in the Green Mountain State has made me change my tune. Vermont just knows how to capitalize on cozy - making me actually look forward to our long New England winters. And that’s really saying something.
I think it’s because Vermonters really enjoy winter. They get out in it. They play. They dress appropriately - so at a little wind chill doesn’t bother them a bit. They aprés with the best of them (which perhaps helps with the warmth factor). They gather around large fireplaces for hours and just enjoy the company they keep. They cook. They hygge. You see what I mean, they embrace it. And I’ve learned that’s what it really all comes down to.
Vermont is the kind of place where you can almost hear corks pop (or perhaps beer cans snap…whatever your preference) when a big snow storm is announced. The entire state just can’t wait to get out and play. I love that. You won’t hear the complaints like you do in the rest of the region - instead, you can feel the anticipation vibrating through the mountains. Like multiple Christmas mornings all winter long. People of all ages unwrapping the gift of snow.
So where should you stay to get down to embracing the winter charm in Southern Vermont? Here are some of our favorite digs that feel like home.
A picture perfect inn just outside of a Manchester. It feels like home, if your home was a stunning farmhouse with beautiful views. Insider tip: don’t miss the breakfasts!
Right in the heart of Manchester, this beautiful Inn is hard to miss with it’s gorgeous red barn facade. Warm and inviting innkeepers just make it all that much more charming.
This cozy little Inn in the sweet town of Dorset has a true Vermont feel and a great little restaurant too. We particularly love sitting by the fireplace in the bar.
A sweet Relais & Chateaux property tucked in the hills, this property truly embraces the need to stop and just savor your surroundings.
Beautifully decorated with every detail considered this beautiful (dog friendly!) hotel is also home to one of our favorite restaurants in the area - The Copper Grouse.
A Manchester original, The Equinox has been part of the area’s scene for ages. We particularly love the spa, grabbing drinks around the fireplace, & the trails in the back!
Another Dorset gem, the Barrow’s House is tad more modern in its approach, yet still so Vermont. Even if you don’t stay here, we love the Tap Room.
In the charming town of Bennington, Four Chimneys Inn combines the old world charm with everything you could possibly need to enjoy your Vermont stay.
Now, one of the most important things about keeping warm during the winter months, and in Vermont in particular, is the food. You can’t spend a weekend hunkered down without a proper menu in place, and luckily this region of Vermont has your cozy cuisine covered. From casual to special occasion (don’t worry - snow boots are still welcome), we are never disappointed when we sit down at these tables.
CASUAL EATS - BREAKFAST / LUNCH / DINNER
Part general store, part bar, part great eats - there isn’t a thing you want that isn’t at J.J. Hapgoods.
A renovated gas station turned amazing spot for delicious eats. Indoor and outdoor seating.
The breakfast spot in town - this tiny little spot is big on flavor - and portion sizing!
Classic diner serving up serious comfort food. Nothing fancy, but absolutely perfect.
Great spot for delicious soups and sandwiches. Named after their old golden retriever (so you know I love it).
Looking for something a tad different? This spot in Manchester is just the ticket.
CASUAL EATS - ON STRATTON MOUNTAIN
A tad more upscale than your typical ski bar scene with an interesting menu. Gigi & Mike at the bar are the best!
What you think of when it comes to a ski bar. Head downstairs to Green Door Pub after.
Aprés ski headquarters. Even better when the deck is open and the sun is shining. Get the nachos.
Recently reopened, Johnny Seesaws should be on everyone’s must eat list when visiting the area.
A great gathering spot right on Main Street in Manchester. Fun ambience and menu.
Classic and old school Vermont with a cozy dining room and a menu filled with comfort food.
Award winning wine list and steaks - it’s easy to see why this place has been a Manchester tradition for years.
Grab a seat by the window to take in the amazing food and lovely views.
A true farm to table experience we are lucky to have in the area. Warm and inviting, with a ever-changing menu.
A husband and wife duo make this tiny restaurant burst at the seams with flavor.
Curl up next to the fireplace or belly up to the bar, this chic little spot is hard to beat..
A newbie to the Manchester scene, great beer menu and overall vibe.
A Manchester mainstay, the Reluctant Panther is known for its award wining cuisine.
Picture perfect bridge outside of Manchester - be sure to avoid the dollar fine!
Located in West Arlington, this darling bridge leads into the old homestead of Norman Rockwell.
A great place to bring kids, this family friendly farm has loads of friendly animals, and a great cheese selection!
Although more popular in the summer and fall months, the trails are magic when covered in snow.
Scenic in all seasons, the Equinox Pond is particularly spectacular in winter.
Hildene’s stunning walking trails become a perfect place for cross country skiing.
Southern Vermont’s highest peak with something for everyone. Great village for skiers and snow bunnies alike.
Family friendly and great terrain, nicknamed the “Sun Mountain” for it’s southern exposure. .
Old school in the best possible way, Magic has personality and is a true Vermont experience. .
Miles of stunning trails with a knowledgeable and passionate staff to help in anyway.
My all time favorite bookstore. Wood floors and helpful staff, a beautiful bookstore with loads of nostalgia.
Everything you could possibly need for your outdoor apparel no matter what the season.
Nothing like a antique store in Vermont. This one always has fun finds.
A beautiful store that just so happens to be dog friendly. They carry everything from home to sport.
One must include the country store of all country stores when doing a shopping round up!
A great little brewery to pop in and pick up all your beverage needs.
All the little things about Vermont you just love from cast iron skillets to maple syrup.
Beautiful woodworking that make for the perfect piece of Vermont to bring home.
I think what I love most about winter in Vermont is the excuse to slow down. To slow way down. It encourages me to make the little things like grabbing a great cup of coffee or gathering around a fire a true event in the day. It’s embracing that first breath of crisp mountain air. Or lingering over a breakfast with way too much maple syrup. It’s all the little memories we are making when we don’t even realize it - which is the greatest gift a season could ever give.