2019 Dates Will Be Announced Soon

Already united by a common sense of place known as The Shires of Vermont, history, and culture, this beautiful region between the Taconic Range and the Green Mountains also possesses abundant recreational resources, a proud agricultural heritage, and a robust entrepreneurial spirit. A wide range of culinary, lodging, and shopping experiences await curious travelers along our highways, byways, and country roads, and on our mountainsides and busy Main Streets.

Surrounded by mountains and enriched by the many waterways, including the Battenkill and Walloomsac, Bennington has preserved what most of America has sacrificed: a thriving community center with a rich history, stunning architecture, locally owned shops, and small-town hospitality.

The people of Bennington look forward to welcoming you to this place we call home.

The Stay to Stay Weekend in August also coincides with the annual Bennington Arts Weekend. Be sure to check out these main events:

  • Downtown First Fridays
  • 4th annual Homebrew Festival (Saturday)
  • Southern Vermont Arts and Craft Festival (Saturday and Sunday)


Friday Evening

Welcome Reception will take place 4–6 p.m. at the Downtown Welcome Center
215 South Street
Bennington, Vermont 05201
(802) 442-5758

Saturday & Sunday

These are your days for exploring.

Experience Downtown Bennington's many shops, restaurants, and sidewalk cafés. Enjoy a vibrant cultural scene in the Arts District with live theater, art galleries, museums, and Vermont’s largest downtown Wi-Fi network. Walk along the Riverwalk, stop by the robust farmers market and stock up at Vermont’s largest arts supply store.

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 a co-maker or incubator space.


Monday, from 10 a.m.–1 p.m. at Southwestern Medical Center
100 Hospital Drive
Bennington, VT 05201

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


Monday, from 10 a.m.–1 p.m. at KW Vermont - Brenda Jones Real Estate Group
219 North Street
Bennington, VT 05201


Monday, from 10 a.m.–1 p.m. at the The Lightning Jar
194 North Street
Bennington, VT 05201

If you plan to attend the upcoming Stay to Stay Weekend in August, please fill out the form below and we will reach out to discuss your weekend details.

If you are interested in participating, but cannot attend the upcoming Stay to Stay Weekend, scroll to the bottom of the page and subscribe to receive information on future weekend dates. This will ensure you're in the know for future Stay to Stay Weekends in Vermont.


The deadline to sign up for the August weekend is August 3rd.

The Bennington Area Chamber of Commerce logo.


The Bennington Area Chamber of Commerce promotes, leads, and advocates a unified effort, on behalf of its members, to maintain and improve a healthy business climate and rewarding quality of life.


Guests who sign up for the August Stay to Stay weekend will receive a 25% discount on Sunday’s night stay.

Knotty Pine Motel
(802) 442-5487
130 Northside Drive, Bennington, VT 05201

Hampton Inn Bennington
(802) 440-9862
51 Hannaford Square, Bennington, Vermont, 05201

Four Chimneys
(802) 447-3500
21 West Road Bennington, VT 05201

The Hardwood Hill
(802) 442-6278
864 Harwood Hill Road, Bennington, VT 05201

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.


Hotel Brooks in Brattleboro, Vermont.


June 14–17, August 9–12, and 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.

Rutland Regional Chamber of Commerce Building


June 21–24, August 9–12, and 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.