Located in southern Vermont in Windsor County, Woodstock is an archetypal New England town, complete with covered bridges, 19th century homes and an authentic pastoral feel. As such, this destination has consistently been ranked one of the most beautiful small towns in America.

GETTING THERE

If you have a car, Woodstock is a fairly easy drive from major Northeastern cities. From Boston, you can make it there in 2.5 hours, while the trip from NYC will take about 4.5 hours, depending on traffic.

Amtrak also operates trains north to White River Junction, VT which is only a 20 minute drive to Woodstock. The scenery is beautiful but the trip is a bit long from NYC and departure times are limited. For the quickest route, Cape Air runs daily trips from Boston and NYC (Westchester) into Lebanon, NH, which is only a 30 minute drive to Woodstock. The airport in Lebanon is quite small, but it does have rental cars on premises. If you arrive in Woodstock by train or plane, I definitely recommend renting a car to drive around the area.

WHERE TO STAY

My favorite place to stay is the Woodstock Inn & Resort, which is conveniently located on “the Green” (Woodstock’s main square), just a few minutes from the center of town. Check-out my full review of the Inn here.

For a less expensive option, The Shire Hotel at the other end of town offers spacious and modern accommodations. And for those looking for more of a homey experience, there are plenty of B&Bs in Woodstock to choose from.

WHERE TO DINE

1. The Red Rooster – The main restaurant in the Woodstock Inn is one of the top places to dine in Woodstock, featuring craft cocktails and farm-fresh cuisine. I always recommend dining here for lunch or dinner (or both!).

 

2. The Mill at Simon Pearce – Located in nearby Quechee, Vermont, diners can visit the Simon Pearce glassblowing workshop and purchase one-of-a-kind glassware in the shop before and after dinner. The restaurant itself offers beautiful views of the Quechee Gorge and the menu features innovative American cuisine with fresh local ingredients. This is a more upscale dining experience and is perfect for a celebratory or romantic dinner.

3. The Prince & The Pauper – Featuring regional cuisine, The Prince & The Pauper is located in the center of town within an easy walking distance from any of the aforementioned accommodations. The cozy atmosphere is perfect for an intimate dinner on a chilly evening.

4. Cloudland Farm – On Fridays and Saturdays, Cloudland Farm opens its doors for dinner, with a delicious prix-fixe menu in a rustic setting.

5. The Mountain Creamery – Comfort food at its best. The Mountain Creamery is a Woodstock-favorite. I love their grilled cheese, tuna melts, soups and of course, homemade ice cream.

6. The White Cottage Snack Bar – Just a few minutes outside of town, this summertime favorite is perfect for a post-dinner ice cream cone (ok so I like ice cream).

WHERE TO SHOP

There are so many cute little shops to pop in and out of while strolling along the streets of Woodstock, but here are my top recommendations for local goods:

1. Farmhouse Pottery – Founded 4 years ago by a local Woodstock couple, the Farmhouse Pottery workshop and store is just a short drive from the center of town. Visitors can watch the potters at their craft, while browsing the shop for one of a kind pieces. I may have gone a little overboard with my purchases last trip, but every item is just so beautiful and unique!  The owners have a distinct design aesthetic that I absolutely love and can’t wait to showcase in my own kitchen.

 

2. Simon Pearce – While Simon Pearce now operates retail locations in many major cities, I still love to visit the flagship location in Quechee, VT. The shop features gorgeous handblown glass items handcrafted downstairs by the Simon Pearce team. Visitors can also tour the workshop and watch the glassblowers in action. Simon’s son, Andrew Pearce, also sells his handmade wooden bowls in the shop.

 

3. Yankee Bookshop – Yankee Bookshop is Vermont’s oldest continuously operated bookshop, serving Woodstock since 1935. While I tend to read on my kindle more often than not, I still love browsing a small bookshop and flipping through the new releases or staff favorites. And I never walk out of here empty handed.

4. F.H. Gillingham & Sons General Store – Located just off the main thoroughfare in the town of Woodstock, Gillingham’s General Store is a nostalgic step back in time. The shop was first opened in 1886 by Frank Henry Gillingham, and is still to this day, family-owned and operated. True to its name, Gillingham’s is chock full of everything you could want, from food and wine, to cooking utensils, children’s toys and hardware items. But, the most important purchase for any trip to Gillingham’s is a large jug of Vermont’s own Grade A maple syrup!

5. Woodstock Farmer’s Market – The name evokes a Saturday pop-up of local farmers, but in reality the Woodstock Farmer’s Market is a boutique grocery store with a permanent structure. They offer both a wide selection of prepared foods, as well as a fairly size-able grocery and produce section, with a focus on local products.

WHAT TO DO

If you’re staying at the Woodstock Inn (or frankly, even if you’re not), definitely check out the Activities page of their website for a complete list of area attractions. Below, I’ve also highlighted a couple of my favorite Woodstock experiences.

1. Hiking Mount Tom – Woodstock is definitely an outdoorsy community and so there are plenty of nearby hiking trails to explore. My favorite is to hike to the top of Mount Tom. There are several trails that lead through this nature preserve and a few that head to the top. The trails are challenging but not overly strenuous and once at the top, you will have beautiful views of the valley below including a great bird’s eye view of the town.

2. Hitting the slopes – If you’re visiting Woodstock in the wintertime, there are a couple of options for skiing in the area. The closest mountain is Suicide Six, which is operated by the Woodstock Inn and boasts as one of the oldest ski resorts in the country. For larger mountains, Killington Ski Resort and Okemo Mountain Resort are each about a 30 minute (give or take) drive from Woodstock.

3. Visiting farm animals at Billings Farm & Museum – A favorite for kids of all ages, Billings is a live dairy farm offering families the opportunity to learn about life on a working farm, visit with farm animals and watch farmhands milk the Billings cows. The farm also offers a bunch of special events so definitely check the calendar before your visit.

4. Learning to bake at King Arthur Flour – About a 30 minute drive from Woodstock, sits the town of Hanover, NH (home to Dartmouth College), and just outside of Hanover, is the home of King Arthur Flour. The mecca for any avid baker, King Arthur Flour’s Vermont location includes a cafe (with fresh baked bread and pastries – yum), a store complete with every mix or utensil a baker could dream of, and a baker’s school featuring daily classes. The classes fill up quickly, so definitely book in advance!

I hope you’ll have the chance to visit Woodstock, Vermont soon. This truly is an amazing town with tons of quintessential New England experiences on offer!