The Shires of Vermont

2019 Stay to Stay Weekends

October 25–28, 2019

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 and Manchester have preserved what most of America has sacrificed: a thriving community center with a rich history, stunning architecture, locally owned shops, and small-town hospitality.

Did You Know?

  • In the summer of 2017, Manchester hosted its first annual iTVFest, a film festival for TV executives, producers, and agents. The region also hosted a taping of an episode of “The Bachelor.”
  • In 1856, Charles F. Orvis opened a store dedicated to fly-fishing and related accessories, now known as the Orvis company, which is the oldest operating mail order business in America.
  • The snowboard was invented in 1977 by Jake Burton Carpenter in his Manchester garage.



As a way to "roll out the red carpet" and introduce our Stayers to The Shires of Vermont , we will be hosting a short meet and greet at 5 p.m. at Arlington's Famers' Market on the grounds of the Arlington Inn. A VIP tent will be set aside for Stayers and community leaders with cocktails and light appetizers being served. While perusing the many food delicacies this region offers in an authentic Vermont farmers' market, this is a perfect time to learn more about this specific region of Vermont from the people who know it best!

Come meet with local townspeople and community leaders. RSVP so we get a good count of who is coming.

Afterwards, we encourage you to explore The Shires for a great meal at one of our local dining establishments!

Other Weekend Activities

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.

Manchester is a quaint mountain town with many activities to choose from: fly-fishing in the Battenkill, skiing at nearby Stratton Mountain Resort and Bromley Mountain Resort, browsing in the independent, family-owned Northshire Bookstore, snagging bargains at the outlets stores, visiting downtown merchants, strolling along the marble sidewalks in historic Manchester village, and the list goes on. If you’re simply wanting some peace and quiet, The Spa at the Equinox or the Manchester Riverwalk are two guaranteed ways to help you rejuvenate.

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 and Sunday when employers and incubator spaces are closed, might be a good use of weekend time.

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. Address for the employer reception: Bennington Area Chamber of Commerce; 100 Veterans Memorial Drive Bennington, VT 05201. You can also sign up to meet with a local realtor who can show you potential housing options, visit a co-working or maker space, or visit a child care center. Please RSVP so we can get an accurate number of attendees.


Monday, from 10 a.m.–1 p.m. The employer industry sectors offered include:

Start up
Nonprofit services

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

Co-working/Maker Space

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


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

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.

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.


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.

Hotel Brooks in Brattleboro, Vermont.


October 25–28

Overlooking the Connecticut River, downtown Brattleboro 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


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.

Town of St. Johnsbury


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.

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.