A Winter Weekend in Woodstock, VT

Caroline Morse Teel is the Managing Editor for SmarterTravel Media. Follow her on Instagram @TravelWithCaroline.

Caroline joined Boston-based SmarterTravel in 2011 after living in Ireland, London, and Manhattan. She's traveled to all seven continents, jumped out of planes, and bungeed off bridges in the pursuit of a good story. She loves exploring off-the-beaten path destinations, anything outdoorsy, and all things adventure.

Her stories have also appeared online at USA Today, Business Insider, Huffington Post, Yahoo, Boston.com, TripAdvisor, Buzzfeed, Jetsetter, Oyster, Airfarewatchdog, and others.

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E-mail her at cteel@smartertravel.com.

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Head north (toward colder weather) in the winter—are you crazy? Not if you’re heading to Woodstock, Vermont, a quaint New England town that gets even better in the winter, when a dusting of snow makes everything look magical and the skiing is fabulous. Located less than 2.5 hours from Boston, Woodstock makes for a great weekend getaway, no matter the temperature.

Reserve one of the 142 rooms at the Woodstock Inn, which is more resort than small bed and breakfast. Don’t be in too much of a rush to get to Woodstock Inn though, if you’re journeying up from Boston—there are plenty of reasons to stop along the drive up. Quechee Gorge, nicknamed “Vermont’s Little Grand Canyon,” makes for a scenic photo stop, as does the nearby classic covered bridge.

(Photos: Woodstock Inn)

Beer lover? Make sure that you’re not the designated driver, and stop at Long Trail Brewing Company or Harpoon Brewery for a tour and sample—or just a meal and a cold one. More of a liquor lover? American Crafted Spirits is right across the street from Harpoon, and it happily serves up samples of bourbon, flavored vodka, and moonshine in its cool wooden space. Vermont Spirits is also worth a stop, if only to sample its very Vermont bourbon that is infused with maple syrup.

Once you’ve had your fill, drop off your car at the Woodstock Inn—you won’t need it this weekend, as the inn is located right in the center of town. The recently renovated property was built by the famous Rockefeller family, who carefully preserved the inn’s history while updating it with modern touches. Enjoy a well-crafted cocktail in front of the lobby’s massive fireplace, which attracts guests all hours of the day and night.

Then dive headfirst into the Vermont cheese scene by ordering the cheese fondue appetizer at the inn’s Richardson’s Tavern. A massive pot of melted local cheeses is paired with bread, sausage, apples, and grapes for your dipping pleasure.

We’d say you could work off all that cheese by walking to town, but the walk down the main street takes less than five minutes. If you want to check out the local nightlife, opt for dinner at Bentleys Restaurant—if you linger into the evening on the weekends, you’ll get to see the locals hit the dance floor.

End your night in front of one of the hotel’s three fireplaces, before turning in to the extremely cushy beds for a great sleep.

(Photo: Caroline Morse)

The next day, get up bright and early so you can get in a whole day of skiing. Mon Vert Cafe opens at 8 a.m. every day and serves up a great breakfast. Trust us: Go for the egg, avocado, cheddar, and tomato sandwich on a baguette—you’ll be fueled up for a long day on the slopes. To get to the hotel’s ski slopes, catch the free shuttle, which runs every half hour from the Woodstock Inn.

The hotel owns the intimidatingly named Suicide Six ski area, a small but historical resort (home of the first ski lift in America). The 24-trail resort is perfect for families and novice skiers, as it’s rarely crowded, so there’s plenty of room to learn. Don’t worry, double-black-diamond experts: 30 percent of the runs are for advanced skiers. Stay at Woodstock Inn on a weekday, and you’ll be able to ski for free. If you’re in the market for something a little bigger, Woodstock is also close to famous Vermont ski resorts like Killington and Okemo. We loved the lack of lift lines, the open slopes, and the private-resort feel that Suicide Six offered, though.

Once you’ve skied up an appetite, the slope-side Out of Bounds Restaurant has an indoor/outdoor fireplace and a fun atmosphere. Refreshingly, this resort eatery actually offers up healthy options (like a vegetable and hummus wrap) that are nice changes from the typical heat-lamp hamburgers and pizzas found at most other lodges. The full bar boasts amazingly cheap beer specials ($2 for craft beers) that will make you want to linger here for apres-ski.

When you’re done for the day, take the free shuttle down to the Woodstock Inn’s spa (located about a mile down the road from the hotel), where you can soak in the indoor spa facilities, warm up in the steam room and sauna, or get even more of a workout in the heated pool.

If you haven’t fulfilled your Vermont-cheese quota for the day, you need to hit Brick Oven Trattoria for dinner. The thin-crust margherita pizza is one of the best I’ve had in a very long time (and this is coming from a former New Yorker—high praise indeed). Dine at the bar, where you can chat with the friendly staff about the best things to do in town.

Not tired yet? Burn off the rest of your energy back at the hotel in the brand-new game room. This room is decorated in classic Vermont style, with flannel fabrics everywhere and games carved out of local wood. Snack on the free fresh-popped popcorn and challenge your friends to games of foosball, Connect Four, shuffleboard, pinball, and more. Then relax by the game room’s fireplace and toast to a successful winter weekend in Woodstock.

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