Attend Opening Day at Billings Farm & Museum
What better way to kick off the start of spring than Opening Day at Billings Farm & Museum? On April 4, come experience farm life in the playful “Little Farm Hands” exhibit, while “Art on the Barns” offers an outdoor contemporary art experience. To make the day even sweeter, guests will receive a free scoop of Vermont-made ice cream. Learn more and get tickets here.
Later in the month, don't miss the Baby Farm Animal Celebration, which offers a unique opportunity to get up close with adorable baby farm animals, meet farmers, and experience the wonders of farm life firsthand.
Enjoy New Art Exhibitions at Hall Art Foundation
Starting May 10, the Hall Art Foundation in Reading will welcome visitors to view its program of rotating, temporary exhibitions of contemporary art. See works from acclaimed artists Gladys Nilsson, Joel Sternfeld, and David Wojnarowicz, as well as an American Pop Art Exhibition.
Sample Syrup and Cheese at Sugarbush Farm
Sample cheese and maple syrup, visit the farmhouse gift shop, and explore nature trails at Sugarbush Farm. This scenic farm has been in the same family for generations.
Come to Bookstock, the Vermont Festival of Words
Bookstock, the Vermont Festival of Words, will return to Woodstock May 16-18. Join on The Green and around the scenic village of Woodstock for Bookstock's famous book sale of almost-new and charmingly old volumes, including first editions; a poetry festival; hands-on workshops; author readings and presentations; events for children; great food; and many more festivities.
Support Your Favorite Village Shops at the Woodstock Sidewalk Sale
Walk Central and Elm Streets to enjoy outdoor shopping as the village shops open their doors May 16-17 during the Woodstock Sidewalk Sale. Take advantage of excellent sales at some of our favorite local shops. You can find a little something for everyone from beautiful clothing and local artisan made products to homeware and more.
Woodstock is home to an incredible array of unique small businesses and boutiques. Stroll Central and Elm Street for a fun day of shopping, walk a few extra minutes to Mahshu Vintage and Woodstock Consignment, and don't forget to make the short drive to Farmhouse Pottery.
See Cold Chocolate Perform Live at Woodstock Town Hall Theater
Part of Pentangle Arts Vermont After Dark Series, experience the duo Cold Chocolate on May 29, a unique blend of Americana and funky roots music in an unforgettable evening. The lobby opens at 6:30pm for drinks, with the concert starting at 7:30pm. Get tickets here.
Support Local Youth in the Race Around the Lake
Race Around the Lake is held in Barnard, Vermont, on May 18, just 20 minutes from the Woodstock Village. This stunning race loops around Silver Lake through trails in the state park. Runners can choose between a 10K run or a 5K run or walk. Participating in the race is a wonderful opportunity to support a local youth summer and theater program.
Head To The Trails For Mountain Biking
Woodstock, VT has some of the best trails in the state thanks to the Woodstock Mountain Bike Association (WAMBA). Trails typically open in early May. Head to Mt Peg or Aqueduct Trails for great terrain from beginner to experienced. Become a WAMBA member to get special perks, stay in the know, and help support the incredible trail network in Woodstock.
Dine Al Fresco
Longer days and warmer weather means plenty of opportunities for outdoor dining in Woodstock. Enjoy breakfast at Mon Vert or check out the new Dreamscape Cafe. Get coffee at Abracadabra and enjoy beautiful hillside views. Au Comptoir is the place to be for outdoor cocktails. Sandwiches from The Village Butcher or the Farmer’s Market make the perfect lunch on the go at Faulkner Park or The Green. White Cottage opens for the season in May so get some ice cream and enjoy it by the river.
Watch The Memorial Day Parade
Woodstock’s Memorial Day Parade is a beautiful tribute to honor and mourn those who have served our country. Join us in commemoration on May 24 from 10:30-11am. Woodstock’s annual parade highlights the locals who have fought for our freedom.
Cheer on Runners at the Covered Bridges Half Marathon
People come from far and wide to run the Covered Bridges Half Marathon as it is one of the most idyllic races in the country. This race actually sells out within minutes each year. The Half Marathon begins at Saskadena Six in Pomfret, Vermont on June 1 at 8:15am and meanders through the Woodstock Village, along dirt roads parallel to the Ottauquechee River and ends in Quechee, Vermont. The CBHM is always looking for volunteers and cheerleaders. Find a place along the route to cheer on the runners.
Join in the Festivities at Pride of Woodstock VT
Pride of Woodstock is a weekend long event, June 6-8, in celebration of love, diversity and community. This Pride event combines the spirit of Woodstock, Vermont with the vibrant colors of the LGBTQ+ community, creating a unique and welcoming atmosphere for all.
The weekend of events begins on Friday with a Welcome Reception at the Woodstock Inn and a dance party at the Ottauquechee Yacht Club. If running in high heels is more your cup of tea, join us for the High Heel Race on Elm Street on Saturday, June 7 at 10:30am. Check out the Pride of Woodstock event page for more happenings during the weekend including a Craft Fair, Tea Dance, Comedy Show and more.
Soar To New Heights at the Quechee Balloon Festival
The Quechee Balloon Festival, June 20-22, is a popular event and a great kick-off to summer. It is a miraculous sight to behold the colorful balloons scattered across the blue skies of the Upper Valley. Grab tickets to enjoy the festival or book a balloon ride to experience the magic from the air. The festival includes live music, crafts, yummy food and fun activities for the whole family to enjoy.
Watch The Woodstock Alumni Day Parade
The Woodstock Alumni Day Parade always falls the Saturday after graduation. It is a celebration of both the newest Woodstock Union High School graduates as well as all the classes prior. Alumni join forces to create fun themed floats and show their Woodstock pride. Come celebrate our alumni Saturday, June 14 at 2pm.
Enjoy Scenic Views On Woodstock Hiking Trails
Take a short stroll out of the Woodstock Village to hike Mt. Peg. This beautiful trail is a short 1.3 mile loop that takes about 45 minutes to complete. At the top you will get sweeping views of Billings Farm and Killington. This hike is family-friendly and dogs are welcome on leash.
Mt. Tom is another favorite among locals and visitors for the gorgeously maintained trails and stunning scenery. You can begin the hike from Faulkner Park via the switchback trails, the National Park entrance, or Prosper Rd. for carriage trails. Some choose to hike to the Pogue to view the turtles sunbathing on logs and the pristine pond. If you continue beyond the Pogue you can make your way to the summit for epic views of the Woodstock village. This hike is family-friendly. Dogs are welcome on leash.
Treat Yourself to a Spa Day
The Spa at The Woodstock Inn & Resort is the perfect place for some rest and relaxation during your stay in Woodstock this spring. Pamper yourself with a day at the spa enjoying a massage, facial, manicure or pedicure. Be sure to enjoy the amenities including a eucalyptus steam room, sauna, whirl pool and outdoor pool once the weather warms up.
Enjoy Music and Good Food at Feast and Field
A new season of Feast and Field, marks the true beginning of summer in Vermont. Spending Thursday evenings amongst the scenic beauty of Fable Farm in Barnard, Vermont eating farm-fresh tacos and salads, Kiss the Cow Farm ice cream, local brews and wines and excellent live music is the absolute best way to do summer in Vermont.
Find Fresh Veggies, Flowers and Makers at The Market on the Green
The Market on the Green is Woodstock’s weekly outdoor market showcasing local artisan made products, food and beverages. Grab your fill of farm harvested veggies for the week, pick up your local flower CSA, buy artwork from local makers or get wood fired pizza and enjoy live music. The Market on the Green is a Woodstock tradition that brings out the entire community to congregate in support of our local small businesses. The Market on the Green runs every Wednesday from June 4 through October 15, 3-6pm.
See The Beauty Of Spring At Eshqua Bog Natural Area
The Eshqua Bog Natural Area is a 41-acre protected space on Garvin Hill Rd. in Hartland, VT, located 10 minutes from the Woodstock Village. This beautiful botanical wonder features post glacial era bog and fern plants such as the lady slipper, larches and buckbean. May and June are popular times to visit the bog to see the showy Lady Slippers make their big debut. A boardwalk allows visitors to cross the bog and view the lady slippers up close.
