Looking for an alternative to Philadelphia Pride weekend this year? Then Pride of Woodstock might be the event for you. Woodstock, the location of that famous concert you say? No, no, I mean Woodstock, Vermont. Home of Vermont’s only national park (more on that later) and a village so beautiful, it is often voted as one of the prettiest in Vermont. This year, Woodstock is offering its inaugural “Pride of Woodstock” taking place Thursday May 31 to Sunday June 2. Scenic Vermont is a great way to start summer and Pride month!
There are a number of towns/cities in Vermont that host Pride events, but none with an extensive list of events like what is planned here. For a town and village of 3,000 residents, Woodstock is going all in for its first-ever Pride celebrations. The highlight of Pride of Woodstock will be the Drag High Heel Race to take place Saturday morning. First, second and third place will be awarded along with Best Hair, Best Outfit and Best Shoes.
Other planned events include an opening cocktail reception at the Woodstock Inn, LGBTQ+ movies selected by the local high school Queer Straight Alliance, drag brunches, drag trivia, and two scheduled tea dances with DJ Bugie at the East End Park (along the banks of the scenic Ottauquechee River), and an after party at the Village Inn of Woodstock. There will be an arts and crafts fair on the village green and the national park is offering hikes led by park rangers on the trails of Mt. Tom.
Aside from the Pride activities, Woodstock and environs represent the best of what Vermont has to offer visitors to this state. Being a former park ranger, I’ll start the list of must do items with a visit to Vermont’s only national park — Marsh-Billings-Rockefeller National Historical Park located at the northern edge of the village. The park opened in 1998, a gift from Laurence and Mary Rockefeller to the nation. The home (mansion) came into the Rockefeller family through Mary, the granddaughter of Frederick Billings (President of Northern Pacific Railroad). George Perkins Marsh, the previous resident of the property, was the author of Man and Nature (1864) and is considered the founder of the conservation movement. Art lovers should tour the mansion and its amazing collection of Hudson River School paintings. The park has extensive hiking trails that lead to the beautiful Pogue pond and the top of Mt. Tom which has views overlooking the Village.
Adjacent to the national park is the Billings Farm & Museum. Frederick Billings hired farm manager George Aiken in 1884 who established the herd of Jerseys. The farm today offers great exhibits, milking programs and the opportunity to interact with farm animals including the Jerseys, goats, sheep, chickens, pigs, horses, etc. Don’t miss the award-winning orientation film for both the park and farm, “A Place in the Land” by Charles Guggenheim shown in the Billings Farm Visitor Center.
Just a 20-minute drive away in Cornish, NH is another national park. Saint-Gaudens National Historical Park features the home, beautiful landscaped gardens, studios and works of American sculptor Augustus Saint-Gaudens. Great to visit daytime when the studios are open, but entry is free after 4:30 p.m. and the grounds are great for picnicking and are open to dusk. You will find casts of the sculptor’s works in a maze of tall hemlock/pine hedge rooms including the Shaw Memorial, the Standing Lincoln, Adams Memorial, Farragut Monument and others.
Come for Pride, but if you can’t visit then, Woodstock is truly a year-round destination. If you decide to visit Woodstock, here’s the lowdown on where to sleep, eat and shop. Everything listed here is walkable within the village unless otherwise noted. And be sure to snap your selfie by the covered bridge!
Where to Eat
Mont Verte, 28 Central Street, is a great place to meet up with friends, take a break, and have coffee, breakfast or lunch. They fly the Pride flag year-round! Casual, comfy and rustic seating is available on two floors. The food and beverage served here is almost all organic and sourced locally. This establishment represents Vermont at its best! Two other places for quick take away sandwiches, salads and sweets are Splendid Bakes, found at 4 The Grn, and then there are sandwiches at the deli inside the Village Butcher, 18 Elm Street.
Prince and the Pauper, 24 Elm Street, has been a fixture for dinner in town for years offering classic New England charm, great cocktails, wine list and a dinner menu that includes contemporary to classic. The restaurant also features a beautiful new terrace area for dining outside. Reservations are a must.
Melaza Bistro, 71 Central Street, has a nice atmosphere and great food from a Caribbean inspired menu for dinner.
Not too far of a drive is Simon Pearce Restaurant, 1760 Quechee Main Street, Quechee VT. Located within an old Mill building, the retail and restaurant spaces are beautiful. The food features local ingredients and tables are set using the artisanal handmade blown glassware that you can find for sale in the adjoining rooms. Reservations are a definite must for both lunch and dinner. Ask for a table near the windows that have views overlooking the Ottauquechee River, dam and adjacent covered bridge. In the sales area on the lower level, you can watch the glass blowers at work.
Cloudland Farm is a short drive out of Woodstock along dirt roads into adjacent Pomfret, VT. Cloudland is an authentic Farm to Table restaurant that serves only on Friday and Saturday nights. This place is BYOB with limited menu offerings each week with the beef, poultry and vegetables from the farm itself. Reservations are a must and can be made on the restaurant’s website.
Where to Stay
The Woodstock Inn & Resort is THE place to stay while in town, as it is luxurious and full of history. Bought by Laurence Rockefeller in 1967, the Inn today reflects the substantial investments that the Rockefeller family made over the years into the Village of Woodstock. Amenities of the resort include a spa, fitness center and pool, golf course, Saskadena Six ski area, restaurants and tavern. The Inn is located adjacent to the village green and is hosting the opening reception, gay trivia and drag brunches and is planning a gift bag to those booking a room for the Pride festivities.
The Village Inn of Woodstock is another great place to stay. This B&B inn seasonally flies the Pride flag, and is full of New England character. It features a small bar and eating areas inside along with a great outside terrace for additional dining/drinks and is also the location of the Pride dance after party on Friday evening. Heather the innkeeper is a friend, and often purchases fresh produce and eggs from this author’s farm located just outside the village. Heather is also planning a gift bag for those booking her special Pride packages for the weekend.
Stay at Jimmy’s is a brand-new B&B in town. The place features chic and trendy décor, hot yoga room — with instruction available — and is close to East End Park where the Pride of Woodstock tea dances will be taking place.
If B&Bs are not your thing and the Woodstock Inn is above your price point, then check out The Shire Woodstock, a recently renovated hotel. Some rooms are pet friendly and most include views of the Ottauquechee River.
Shopping & Galleries
Woodstock has numerous cute shops and art galleries to hit between the numerous Pride events. There are one too many to list, but here are a few not to miss:
F. H. Gillingham and Sons, 16 Elm Street, is the quintessential Vermont country store that has just about everything. It has been a fixture establishment in Woodstock forever and features a great authentic country store charm with its old wooden floors.
Forgot an item of clothing? Check out Elevation Clothing, 15 Central Street for great high-quality clothing for all genders.
Be sure to visit the numerous art galleries in the village, including Chip Evans Paintings, 65 Central Street, The Woodstock Gallery, 6 Elm Street, and Focus at 1 the Green just off the Village Green.
Yankee Bookshop, 12 Central Street, is Woodstock’s independent bookstore with an awesome selection of books. Readers should also check out the Norman Williams Public Library next door to the Woodstock Inn. The library features a great interior architecture and reading room, and the foyer has an ongoing used book sale. It promises to have a good selection of LGBTQ+ books on a sale shelf for Pride of Woodstock weekend.
Unicorn, 15 Central Street, is definitely worth stopping in for a minute. Though it is the smallest gift shop in Woodstock, it is chockablock full of fun and beautiful items.
BJ Dunn is a former national park ranger who spent seven years in Philadelphia as Deputy Superintendent at Independence National Historical Park. He frequently recommends Philadelphia as a destination to visit. He is now excited to invite his Philadelphian friends to Vermont for Pride of Woodstock.