Jake and Sara's favorite breakfast and lunch stop in downtown Woodstock. Order ahead to skip the line or eat-in and hangout in their cozy upstairs. A 5-minute walk from both The Woodstock Inn and The Shire.
One of our favorite specialty foods stores between Woodstock and Killington. Stop here to stock up on snacks for your house or hotel room. Or grab a quick sandwich on the way back from skiing at Killington. They also have a reliable, rotating wine and local beer selection.
Great stop on your way into or out of Woodstock for lunch or dinner. The burger is a highlight, but you can't go wrong with anything on the menu. Extensive local beer selection. Reservations suggested, but not required. A 5-minute drive from downtown.
Romantic spot on the Ottauquechee River for lunch or dinner. Don't forget to check out their basement where you can see glass blowers at work. The Whistle Pig tasting room is next door if you're looking for an aperitivo or a nightcap. A 15-minute drive from Woodstock.
The best place in town to get a cocktail (or mocktail!). A cozy, jewel box located a 5-minute walk from The Woodstock Inn and The Shire. Their ginger margarita, la vie en rose, and manhattan black are some of our personal favorites.
Located in The Woodstock Inn. Feels like an old New England tavern. A great option for lunch or dinner if you're staying onsite. Grab a drink from the bar and sit by the fire in the lobby or play a round of backgammon in the library. For those in town on Friday, we'll see you here for welcome drinks!
More than just a brewery! Located a 15-minute drive west of Woodstock, this is a great spot for lunch or on your way back from Killington. It's also a popular stop on the local snowmobile trails if you're feeling that adventurous. They offer live music and elevated pub-fare.
The Beast of the East! There is a trail for every ski level at Killington. Have lunch at Peak Lodge (Sara thinks about their grilled cheese and tomato soup all year round) or the Ledgewood Yurt (a hidden gem behind the learn-to-ski area). With the longest season on the east coast, there is sure to be plenty of skiable acreage in March. A 20-minute drive west of Woodstock.
If you want to get some turns in but don't have time to go all the way to Killington, Saskadena Six is a 5-minute drive from downtown Woodstock. "Mountain" isn't exactly an accurate description of this family-friendly ski area, but it's perfect for a quick morning ride. Owned by the Woodstock Inn, ask them about securing lift tickets.
Downhill skiing not your thing? The Woodstock Nordic Center offers cross country or snowshoeing. Also owned by The Woodstock Inn, they can arrange passes, rentals, and lessons for you. Located a 10-minute walk or 2-minute drive from downtown Woodstock. There's also a shuttle available for guests of the inn.
Indoor activities more your speed? Inn guests have complimentary access to classes and facilities (including an indoor pool) at the Woodstock Athletic Club. Ask for the current schedule at check-in. For those not staying at the inn, you can pay for classes or for day access to the space. Located a 10-minute walk or 2-minute drive from downtown Woodstock. There's also a shuttle available for guests of the inn.
If you're looking to recharge ahead of the festivities, the spa at the Woodstock Inn is not to be missed. It's a luxurious oasis offering a wide range of treatments. Ask about arranging your visit when you make your hotel booking.
Woodstock is a quintessential New England town, home to many local and small businesses. Its worth walking the short stretch of Main Street to check them out for yourself! Some of our favorites include: 37 Central, Woody's Mercantile, F. H. Gillingham & Sons, The Vermont Flannel Company, Clover, Sudie's, RT Home, and Yankee Book Shop.
If you've ever heard Sara talk about Vermont, you've probably also heard her talk about Farmhouse Pottery. Located about a 5-minute drive west of Woodstock, their flagship showroom is not to be missed. The gift shop at the Woodstock Inn also sells a number of their handmade pieces if you're looking to take Vermont home with you.