Traversing Vermont


A weekend away in the Green Mountain State

Every road in the Woodstock area features rolling hills, quaint farmhouses and trees of every color. (Photo by Kimberly Lovisi)

Hot apple cider. Warm flannel. Fresh maple syrup. Aged cheddar. New England Americana. Blazing foliage.

This is what comes to mind when I think of Vermont in the fall. I found all of it and more in the small town of Woodstock, VT, on a recent weekend trip.

The Drive Up

Departing Long Island in a 2019 Chevy Traverse on a Friday afternoon made the five-hour drive as enjoyable as could be. Sirius XM provided the playlist that accompanied the time-honored ombré shift from green to orange alongside the Taconic State Parkway.

Roughly at the midway point to Woodstock is the historic village of Chatham, NY, which I recommend a stop at. Chatham Brewing was a great choice for dinner. The menu extends beyond the typical pub food with seasonal options and a particularly good vegetable chili, and there’s live music on the weekends.

Chevy’s built-in navigation system was incredibly helpful mapping the best route to my destination, but the Traverse easily pairs with Android and Apple smartphones if Google Maps or Waze is your preference. Charging your phone is not a problem with the wireless charging tray and seven, count ‘em, seven USB ports.

The car is also connected to OnStar, which is handy for more than just emergencies. OnStar is like a personal concierge that can give you restaurant recommendations or help you find the nearest rest stop by sending turn-by-turn directions to your car. If you find yourself desperately in need of coffee or a bathroom break, OnStar has you covered.


Woodstock is full of inns and bed & breakfasts, but 506 On The River Inn is especially charming. Nestled beside the Ottaquechee River, the 40-room boutique inn boasts gorgeous views during every season. You’ll never want to leave!

After the long drive, crawling into a comfy bed with fluffy pillows was heaven. Every part of the property is inviting—from the rocking chairs on the patio that overlook the river to sumptuous leather armchairs in the seating areas. Quaint farmhouse décor and antique artifacts welcome guests from every direction.

506 even allows pets in select ground-level rooms. Think of all the smells your dog can smell in Vermont! The Chevy Traverse is just as pet-friendly as the inn, with a spacious interior and seating for up to eight.

In the morning, 506 serves a full country breakfast with scrambled eggs, bacon, sausage, home fries, French toast, oatmeal, yogurt and all the trimmings. It’s out of this world.

Also out of this world is the gorgeous salvaged wood bar. You’ll definitely want to spend some time with a few cocktails or a nice craft beer at that bar. Pro tip: Hot rum and apple cider is the perfect drink on a cool autumn evening.

Finally, make time for a meal at the bistro. The fall menu includes delights like cheddar bacon soup, Bosc pear and blue cheese salad, maple chili wings and local squash & chickpea curry.

Exploring Woodstock

Just down the road from 506 is Central Road, the “Main Street” of Woodstock. The town has a strong Stars Hollow vibe, with a tree-lined courtyard called The Green, stately brick buildings, Colonial style homes, an old church and library—and I haven’t even mentioned the independent shops and eating establishments yet.

There’s a yarn shop called The Whippletree and custom jeweler called N T Ferro. Danforth Pewter offers beautiful handcrafted items and Unicorn is a magical variety store. The Yankee Book Shop is Vermont’s oldest independent bookstore. Not for nothing, but Chevy’s surround vision and backup camera made parallel parking in town a piece of cake. I wondered if strategically placed cameras could really create a virtual bird’s eye view or if the car actually came with its own personal drone.

Finding the perfect souvenir is easy if you spend some time shopping around. I recommend a stop at The Village Butcher for local Vermont products like meats, cheeses and wines. Next door is F.H. Gillingham & Sons, a deceptively large general store that puts Walmart to shame.

No visit to Woodstock is complete without a stop at The Vermont Flannel Company. The small storefront is packed with plaid shirts, hoodies, jackets, blankets, scarves, hats and the list goes on, all made from the softest brushed cotton.

Take a break from shopping at Mon Vert Café for an amazing selection of coffees, teas, breakfast, lunch and bakery items. Ingredients are organic and locally sourced and there are many gluten-free options. Try the butterbeer latte if you’re lucky enough to catch this special seasonal item on the menu.

Even when it’s cold, it’s never too cold for ice cream. That’s where Mountain Creamery comes in. The offerings are all homemade and use farm-fresh local ingredients.

A ways down the road you’ll find the Woodstock Farmers’ Market, which is quite possibly the best place to enjoy all of Vermont’s fall flavors. Its mission is to make fantastic food accessible to everyone. Between fresh organic produce, prepared meals, specialty products, deli provisions and coffee counter, I declare mission accomplished.

Woodstock is a family-friendly destination, so if you’re bringing the kids, plan for at least a half day at Billings Farm & Museum, a nonprofit institution that highlights Vermont’s rural heritage. The 200-acre property is actually an operating dairy farm as well as an educational resource to the community. Kids will love the livestock, children’s programs, workshops, films and fascinating exhibits depicting what life on a farm was like in 1800s. Before you leave it’s essential to hit up the Dairy Bar for Vermont-made ice cream and snacks. (It’s vacation. No one is keeping track of how much ice cream you eat!)

If you venture a bit further in either direction, you’ll find covered bridges in that quintessential Vermont style. Cross the 1836 Taftsville Covered Bridge to get to Sugarbush Farm and see a working maple syrup farm. Quechee Gorge, aka “Vermont’s little Grand Canyon” is not far. Just park in the gift shop lot and walk across the bridge for the best view from above, then pop down the trail to see the gorge from the ground level.

In search of cheese

Cheese is not exactly scarce in Vermont, but Grafton Village Cheese Company makes a mean cheddar that’s worth making a special trip for. Their headquarters are in Grafton, a lovely town with several artist workshops and galleries, antique shopping, a history museum, the Vermont Museum of Mining and Minerals, farms and farmers markets and access to recreation year-round.

MKT Grafton is one place where you’ll find Grafton Village Cheese for sale and a lot more. This modern country store has locally made snacks, wares and tasty sandwiches at the café. However, for the full selection of Grafton’s handmade, raw-milk cheddars, you’ll want to visit the Brattleboro retail store.

On a chilly autumn day, it was such a pleasure to have heated seats and steering wheel in the Traverse. You don’t even know what a luxury this is until you have it and realize cold fingers are a thing of the past!

Navigating the winding roads of Vermont once the sun goes down can be challenging, but the Traverse’s lane assist feature really does work! If you start to drift out of your lane, the car gently nudges you back into it. Between lane assist and collision alert, which alerts you when other cars are getting too close, these features are more than just convenient, they are potentially life-saving.


Make Grafton Village Cheese Company your first stop in Brattleboro.

On the way back to Long Island, your route will likely take you through Brattleboro, an awesome town in southern Vermont worthy of a separate vacation.

Start with the Grafton Village Cheese Company where you can not only pick up edible souvenirs from your trip, but also watch cheese being made and learn more about the cheesemaking process. Did you know cheddar is a verb? The building is right next door to Retreat Farm, another historic farmstead you can easily spend the better part of a day exploring and another day on the woodland interpretive nature trails.

In town, there are old bookstores, bike shops for adventurers and a bunch of offbeat independent shops and restaurants.

This place is home to a tiny house festival, an international puppet festival, various food, drink and music festivals throughout the year and the “Strolling of the Heifers”—if that doesn’t pique your interest, what would?

Vermont is the ideal vacation destination from New York in the fall. I’m certain to return for beautiful scenery, engaging activities and delicious things to eat. So long for now, Vermont!


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