September 13–16, 2019

Named one of the “most beautiful towns in America,” Woodstock is brimming with New England charm and sprawling bucolic vistas. Stroll through the village for your pick of historic shops – from boutiques and restaurants to art galleries, a general store, and movie theatre – nearly all locally owned. Want a taste of the outdoors? Set your sights on the only national park in Vermont, just steps away from bustling Central Street, or visit Woodstock’s three historic covered bridges. And with an expansive trail network offering hiking, mountain biking, horseback riding, skiing, and snowshoeing access, outdoor recreation is a year-round occupation.

Experience for yourself the local farm-to-table cuisine, picturesque beauty, ski areas, golf courses, and thriving arts community that draw visitors from near and far. As part of your Stay to Stay Weekend, you can take it a step further, learning why many choose to make Woodstock their home: the welcoming community, outstanding school system, proximity to Dartmouth-Hitchcock Medical Center and Dartmouth College, and housing prices that are a pleasant surprise to anyone hailing from local metro areas.

This weekend is a special Mountain Biking Stay to Stay Weekend. Visitors can participate in multiple rides and tours available for every skill level. See below for details.

Did you know?

  • Woodstock is the only town in America with six church bells cast by Paul Revere & Company.
  • There are no stop lights in Woodstock – and thanks to the Rockefeller family, who helped preserve the town’s historic architecture, the village’s power lines are buried underground.
  • The town maintains a free community wifi internet service that covers most of the village, dubbed "Wireless Woodstock."


Welcome Reception

We are gathering on Friday, September 13 from 5-7 p.m. at 506 on the River Inn.

1653 U.S. Route 4
West Woodstock Rd.,
Woodstock, Vermont

Join us to talk with community members about what it is like to live and work in the heart of  Vermont. If you plan on attending our welcome reception, please RSVP here, and you’ll receive location details.

Weekend Activities

Not a mountain biker? Use Saturday and Sunday to explore the community and its many attractions at your leisure.

To take full advantage of the many resources available to you throughout the Weekend, we encourage you to connect with the community and business leaders you meet at the reception event and make plans with them for additional conversation and introductions. Scheduling a visit with a local realtor on Saturday or Sunday when employers and coworking spaces are closed might be a good use of weekend time.

Mountain Biking and Gravel Rides

For all rides, bring water, a snack, and your helmet, and of course make sure your bike is ready to ride. If you are looking to rent a bike, check out rentals from Woodstock Sports or Suicide 6 Bike Park.


Beginner MTB Group Ride – 3 pm at the Aqueduct Trails located off Cox District Road in West Woodstock

Newer to mountain biking, or simply looking for a more low key option? Join WAMBA on a 1.5 hour tour of the Aqueduct Trails. This will be a no-drop ride. Please RSVP if you plan to ride with us.

Gravel Grind – 10 am at the Woodstock Green located in the heart of town on Route 4

Feel the need to explore the miles and miles of dirt roads around Woodstock? Join the gravel grinders for a moderate 15-20 mile ride. Expect plenty of hills. Please RSVP if you plan to ride with us.

Advanced MTB Group Ride – 10 am at the Knox Meadow Parking lot for the Mt. Peg Trails; located down Route 106 just past the Resort’s Nordic Center. Free passes for the Mt. Peg Trails are available to Stay to Stay Weekend participants. To find out how to get yours, check in with your hosts at the Friday evening reception for instructions.

Looking to get a taste of the intermediate to advanced trails at Mt. Peg? Join WAMBA for a 2 – 2.5 hour tour of the Mt. Peg Trails. Bring your legs and lungs — this will be a faster paced ride for skilled riders. Please RSVP if you plan to ride with us.


Family Ride – 9:30 am at the Aqueduct Trails located off Cox District Road in West Woodstock

Join us for our regular weekly Family Ride. Typical rides are approximately 1.5 - 2 hours in total. We warm up on the pump track and then work our way up to the reservoir. Based on who shows up we will split up the skill levels so everyone has fun and can learn and progress their skills. Please RSVP if you plan to ride with us.

For Serious Riders

Stay to Stay Weekend participants can experience Suicide 6 Bike Park, hosting a variety of flow trails and technical descents, plus a progressive skills loop, a strider park for the little ones, and a bike shop.

Though not part of the Stay to Stay Weekend activities, the Woodstock Enduro Adventure Ride is an an epic tour of the area's growing trail networks which covers 25+ miles and nearly 4000ft of climbing.  For those wanting to push themselves on the way down, there will multiple Strava based enduro segments throughout the course. To learn more about the ride, check out WAMBA’s calendar of events.

Monday Morning Networking

Wrap up your weekend with a solid sense of the employment opportunities in the region. Monday morning is your chance to meet with employers in specific sectors and with business owners who can discuss what it’s like to work in the community. You can also sign up to meet with a local realtor who can show you potential housing options, or to visit our two coworking spaces and commercial kitchen food hub.

Coffee & Conversations

Monday, at 8–9:30 a.m. at the The Woodstock Inn and Resort
14 The Green
Woodstock, VT 05091


Monday, 8:00 a.m.-9:30 p.m. The employer industry sectors offered include:


If you would like to meet with an employer in a different industry, please indicate your preference in the form below.


Monday, at 10:00 a.m. at Williamson Group Sotheby’s International Realty
24 Elm Street
Woodstock, VT 05091

Co-working/Maker Space

Monday, 9:30 a.m. at the Optimist Center
65 Central Street
Woodstock, VT 05091

Monday tours of the The Schoolhouse by appointment
46 Lincoln Corners Way
Woodstock, VT 05091

Vermont Kitchen, tours by appointment

Visit Child Care Centers

Rainbow Playschool, tours by appointment, 281 North Barnard Road, Woodstock, VT 05091


The deadline to register is one week prior to the first day of each weekend.

Woodstock Vermont Area Chamber of Commerce

Woodstock Area Chamber of Commerce

The Woodstock Area Chamber of Commerce is a membership organization whose purpose is to connect member business organizations with community and visitors, promoting the region as a great place to live, work, and play.

Woodstock Area Mountain Bike Association

Woodstock Area Mountain Bike Association

Founded in 2016, the Woodstock Area Mountain Bike Association (WAMBA), a chapter of the Vermont Mountain Biking Association, is a non-profit organization dedicated to developing and increasing access to sustainable mountain bike trails in and around Woodstock.

Woodstock Vermont Economic Development Commission

Woodstock Economic Development Commission

Founded in 2016, the goal of the Woodstock Economic Development Commission is to plan and implement sustainable economic development in the Woodstock area.


Whatever brings you here, Woodstock’s welcoming charm will keep you staying here. Enjoy the warm ambiance and amenities at any of our lodging properties, no matter your budget. From independently owned motels to all-inclusive resorts; or historic inns to rustic camping, you’ll find a place to make your stay even more memorable. Explore the options in Woodstock.

Frequently Asked Questions for Stay to Stay Weekend.

Questions about Stay to Stay Weekends?

Thinking about signing up for a Stay to Stay Weekend but have some questions first? Please read these frequently asked questions.


Rutland Regional Chamber of Commerce Building


October 18–21

Welcome to the real Rutland County — a colorful combination of country roads, quaint villages, and historic downtown centers in the heart of Vermont’s Green Mountains.

Downtown Newport overlooking Lake Memphremagog.


December 13–16

Just south of the Canadian border, welcoming Newport straddles cultures and waterways. This small city, perched on jewel-like Lake Memphremagog, is surrounded by natural beauty and vast recreational opportunities.

Town of St. Johnsbury


September 13–16 and October 4–7

The southern gateway to the beautiful Northeast Kingdom, St. Johnsbury and its environs offer culture, recreation, delicious food, and modern amenities, combining economic opportunity with a rich quality of life.

The Equinox in Manchester, Vermont.


September 13–16 and October 25–28, 2019

Bennington and Manchester are located in the beautiful region between the Taconic Range and the Green Mountains.

Hotel Brooks in Brattleboro, Vermont.


October 25–28

Overlooking the Connecticut River, this downtown is lined with buildings that house galleries, restaurants, shops, breweries, and a 1938 art deco hotel and movie theater.

A sunset over Lake Champlain from the Burlington waterfront.


November 8–11

Compact and beautiful, Burlington is home to a thriving arts scene, creative entrepreneurship, great shopping, three colleges and a university, and a full range of four-season outdoor pursuits.