Vermont is an enchanting destination – featuring the beautiful rolling Green Mountains and charming small towns. While many visit for the fall colors, experiencing Vermont in November offers a unique perspective on the state’s famous craft brewery scene, it’s ski resorts, maple syrup, and artisanal cheese. Gift shops sell all these items – either in physical form or a depiction – and they have become synonymous with this beautiful New England state.
Peak foliage had faded by November, and there is a sereneness that can only exist in the late autumn months in these wonderful mountain towns. The local cheese remains sharp and delicious, and the landscapes often linger with a dusting of frost or early snow, showing promises of the winter to come. The crisp mountain air mixes with the scent of wood smoke, and delivers cozy feelings.
November is quiet season in Vermont, where many establishments close for a few weeks to buffer the autumn and winter rushes. The quiet is what always attracts me to visit, and the budget goes further. Not everywhere will be open, so check ahead as many shops, hotels and restaurants close for a few weeks in November to reset and prepare for the winter.
It’s a fantastic destination for a weekend escape from the bustle of Massachusetts. This particular trip was a special one, as we were celebrating our wedding anniversary, which is a great excuse to spend a week away in New England (like our previous weekend in Maine in November trip). Although we had visited Vermont once before, we had a different itinerary this time, focused on food and a slow pace to allow us to explore freely.
We packed our bags and left the routine behind, heading north on the scenic back roads for our long weekend in the heart of Vermont.
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Saturday – Ludlow & Killington
On Saturday we headed north from central Massachusetts via the country back roads, which gave us a spectacular view of the countryside, to kick off our weekend in Vermont in November. Normally we head up I-91 and into Brattleboro, but after a few disappointing visits to that town in the past few years, we opted to skip it and headed towards Ludlow instead. Brattleboro used to be our favorite, with a fantastic cheese shop, good brewery, a walk-able downtown, nearby covered bridge; but in recent years much of the town has felt closed and our favorites like Grafton Cheese and Whetstone Station had closed and moved on.
Grafton Cheese Shop
As we were nearing Ludlow we spotted a familiar looking logo – our favorite cheese shop, the one from Brattleboro that had closed. Making a quick, and safe, U-turn we were gleeful to enter our longtime favorite Grafton Cheese Shop. Although the brand could be found in Massachusetts we always adored visiting their quaint country store for free samples, and the inevitable cheese purchases. For us it was a sign that we were on the right track for a fantastic weekend in Vermont.
It may have derailed our plans of spending more time wandering in Ludlow, but for us it was well worth it. We purchased several of their fantastic cheese, and a few additional gifts from their well stocked shop. The staff are always incredibly friendly and so happy to cut you off a piece of cheese from any of the wheels on display – so beyond the main offerings we also got to try an a few special cheese as well.
Our visit to Ludlow was shorter than intended, and we’d love to go back. The town was absolutely charming, despite the turn in the weather, and has a fantastic central area. And a great beer shop carrying lots of local craft brews from across Vermont. We picked up a few of the beers to try and carried on to our hotel.
Tasting at Killington Distillery
I had chosen the Killington Mountain Inn specifically for this trip because it not only has amazing views of Killington Mountain, but also is home to the Killington Distillery. Our anniversary fell during the quiet part of their season – after the rush of leaf peepers and before the rush of skiers – and many places in the area were closed, including the restaurant and distillery. However, the incredible staff at the Killington Mountain Inn had arranged a private tour for our anniversary trip, which went above and beyond and provided us a fantastic view into their offerings.
The Distillery had a wide variety of craft spirits on offer – including Vodka, Tequila, Gin, Rum and Whiskey. What impressed me most was the passion and artistry that went into everything from the spirit itself, local ingredients, the labels, and the entire experience. These award winning spirits were what inspired our weekend trip, and they were fantastic. We were regaled with stories from one of the owners, JP, and learned a lot about what makes these spirits so special. It was easy to see why these spirits are award winners, and why guests drive for hours just to collect a case or a few bottles.
Since we were “off season” many of the restaurants were closed. The team at the Killington Mountain Inn explained that there’s roughly a 4 week period where the restaurant and business shut down for 2 weeks at a time to give the staff some time off and a chance for them to clean and prep for winter.
Thankfully The Foundary, one of the local restaurants, was open. The quaint atmosphere and the incredible menu made for a fantastic evening out, after our morning of travel, and afternoon of tastings.
Sunday – Woodstock
There’s nothing like spending a weekend in Vermont in November and waking up to a beautiful dusting of snow in the morning. It was entirely unexpected and a spectacular way to start the day, especially with our incredible view of Killington Mountain.
We enjoyed the continental breakfast at the Killington Mountain Inn before hitting the road for a day of exploring central Vermont. Central Vermont has a large variety of places to visit, and even though we had spent a weekend here previously there was still much more left to be seen.
Woodstock
Woodstock was our first destination, known to be quaint and charming (if a bit upscale). Just outside of Woodstock we first stumbled upon the Woodstock Farmers’ Market, which was a fabulous find. With a variety of fresh food and local offerings we grabbed a few fresh desserts from the bakery and a freshly pressed apple cider. Although it was busy I was impressed at how quickly the team there served all the customers and kept everything moving and stocked up.
As we parked up in Woodstock a fine misty rain began to descend, but that didn’t stop the other visitors from wandering the streets and ducking into the shops for a brief reprieve. Where I had expected something a tad more rustic it was quickly clear that this town was meant to cater to upscale guests, probably from New York, with it’s fancy boutiques and overpriced cafes. Even so we enjoyed the window shopping, and our hot drinks (on a cold wet day) from the popular Mon Vert Cafe.
Sugarbush Farm
From Woodstock we carried on for a brief stop at the incredibly picturesque Historic Taftsville Covered Bridge, before carry on through the beautiful winding mountain roads before we reached our next stop at the Sugbarbush Farm. The drive was truly an essential Vermont experience; with the mist occasionally rising through the mountains, winding through wooded lanes with glimpses of mountains and valleys.
The farm was a last minute addition to the itinerary, but glad that the researched payed off. The farm produces both maple sugar and cheese, two of our favorite things to enjoy from Vermont. Mapling is done at a specific time of year, during the brief window when freezing nights are followed by thawing days to trigger the sap flow, and ends once the maple trees begin to bud. As such we were not even close to experience mapling first hand, but they had a fantastic display that depicted how maple is harvested and boiled down into the maple syrup we know and love; this display was set in their quaint mapling house which provided a gorgeous backdrop to the misty mountains as we wandered around the farm.
Inside the primary building they also showed how cheese was made and offered samples. This was particularly enjoyable as well and all the hosts were very knowledgeable about the process. Melted wax was on the walls, where they had been wrapping cheese earlier in the day most likely, and it had a unique atmosphere from among the different cheese makers we visited. We added several of the Sugarbush cheese offerings to our cheese haul from the previous day, and already suspected it would grow more before we departed Vermont.
Brewery Visits
From Sugarbush Farm we headed east so we could visit a few local breweries. As it was a Sunday they were closing early but we had two in mind that we hoped to make it across to. On the way we found the home of Simon Pearce, and stopped in briefly to watch the glass blowers at work. The artisans at work were impressive to witness, and the wide variety of offerings at the shop were something to behold.
Vermont is well known for it’s craft breweries, and I had picked out the nearby River Roost Brewery for our first visit. Located in Hartford, near the border with New Hampshire and the White River, it was a fantastic find. The tap room was easy to find and had a fantastic ambience, with a wide variety of beer it was a great brief stop on our journey through central Vermont. River Roost Brewery’s offering had some signature styles, including the fantastic Mas Verde.
Next we headed a little south from Hartford Vermont to Harpoon Brewery. I’ve previously visited their Boston location, which I highly recommended in my Guide to Boston article, and consider them to be one of the better craft breweries in New England. We stopped here for dinner and to taste several of their beers, focusing on the seasonal offerings since we were already familiar with their wider range. It was such a fun visit, with a great local live musician playing all night, the brewery floor on display, and a great gift shop full of unique finds. We really enjoyed the visit, the food, and the general setting.
Monday – The Road Home
Monday was the end of our long weekend in Vermont in November, and we had planned to traverse the back roads once more to experience all that Vermont had to offer. It was another cold and rainy morning in Vermont, and unlike Sunday there was no snow to enjoy.
Sugar & Spice
Many years ago I had done a Vermont weekend with a friend of mine, and we had stumbled upon Sugar & Spice. It was a great breakfast spot offering all kinds of delicious breakfast items that pair well with maple syrup. It is such a quintessential Vermont staple that I knew we would have to visit it on our last day in Vermont. The rustic building, with a two-story open gallery overlooking a maple boiling vat, is has such a unique vibe. We really enjoyed the visit, and their signature “Sugar & Spice” pancakes.
While we thoroughly enjoyed the cozy atmosphere and hearty flavors here, we couldn’t help but compare the experience to our frequent visits to Polly’s Pancake Parlor in New Hampshire, which remains one of our all-time favorite ways to experience New England.
Plymouth Cheese
Plymouth Cheese is a well known brand in New England; it’s readily available at the major supermarket in my town. It’s a beautiful wax covered cheese with a variety of flavors, but usually a focus on cheddar. While we were touring this area of Vermont we realized that the home of Plymouth Cheese was close by. We detoured on our way out of Vermont to have a brief visit and taste their array of cheese.
What I didn’t expect to find there was a small museum. It offered a fascinating look into American history through one of the oldest cheese factories in the United States. But more interesting than that alone was the fact that it was founded by the father of President Coolidge in 1890. We were able to explore the on-site cheese making museum, which had original equipment and artifacts that illustrated the evolution of cheese making in Vermont.
Snow Republic Brewery
We drove back through West Dover, Vermont – home to Mount Snow – and discovered the charming Snow Republic Brewery. With it’s fabulous “apres ski” vibe we really liked this cute log-cabin style building, with the funky and welcoming interior, and a fantastic line up of craft beers on tap. We grabbed a small bite and a flight to share and were impressed with both, which made for a perfect short visit on our way south through Vermont and back into Massachusetts.
Scenic Drive back to Massachusetts
The winding drive back through Vermont, passing through the charming town of Wilmington, provided a beautiful scenic route. After leaving central Vermont we jumped on Rt-110 and followed it back down to the Massachusetts border. Despite the wet weekend we had a wonderful trip and want to spend more time exploring some of the smaller Vermont towns that offer a quaint and quiet place to visit.
Our Slow-Paced Food & Brewery Itinerary for Vermont in November
Here is our itinerary, focused on cheese, small towns and breweries. If you’re planing your own escape this may help give you some ideas for what is fun to visit. This route was designed for a long weekend and prioritized flavor and atmosphere at a slow pace through the back roads of Vermont.
Day 1: Spirits and Lakeside Charm in Ludlow & Killington
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Morning: Start your journey in the charming town of Ludlow, the heart of the Okemo Valley. It’s the perfect place to grab a coffee and feel the transition from autumn to winter.
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Afternoon:
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Artisanal Stops: Head to the Grafton Village Cheese Shop to sample their world-renowned extra-sharp cheddar and specialty cave-aged wheels.
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Après-Style Afternoon: Visit Killington Distillery for a tasting of their award-winning Woodland Gin or Maple Cask Bourbon, soaking in that “mountain mindset.”
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Evening: End your first day at The Foundry at Summit Pond. The atmosphere here is quintessential Vermont—refined yet rustic, overlooking the water.
Day 2: Covered Bridges and Craft Hops in Woodstock
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Morning: Begin at the Woodstock Farmers’ Market (a year-round staple) to stock up on local provisions before exploring the boutique-lined streets of Woodstock.
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Scenic Icons: Take a detour to the Historic Taftsville Covered Bridge, one of the oldest and most photographed bridges in the state, looking particularly striking against the November frost.
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Farmstead Cheese: Wind your way up to Sugarbush Farm for a walk through the maple groves and a sampling of their famous smoked cheeses.
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- Evening: Head toward the New Hampshire border for a “hop-heavy” afternoon. Start with the hazy IPAs at River Roost Brewery in White River Junction, then finish with a flight and a soft pretzel at the expansive Harpoon Brewery in Windsor.
Day 3: History, Heritage, and the Journey South
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Morning: Kick off your final day at Sugar & Spice in Mendon. It’s a working sugarhouse where the pancakes are legendary (and arguably give our favorites at Polly’s in NH a run for their money!).
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Afternoon:
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Stop at Plymouth Cheese, located at the Calvin Coolidge State Historic Site. It was founded by the President’s father in 1890 and features a fascinating cheesemaking museum.
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Final Pints: As you head south, stop at Snow Republic Brewery in West Dover for a casual “West Coast meets Vermont” vibe and a pint of Hop Avalanche.
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Wilmington Wander: Finish your trip in the historic village of Wilmington. It’s the perfect final stop to browse the local shops and enjoy the crisp mountain air before heading back home.
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