The Shires of Vermont

2019 Stay to Stay Weekends

September 13–16 and 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.


Welcome & Rides

Saturday Ride

When: Saturday, September 14 at 11 a.m.

Where: Camelot Village, 66 Colgate Heights, Bennington, VT 05201


The Bennington Area Trail System will host a ride on Saturday morning from 11 am to 2 pm with a lunch to follow.

Please plan to meet at Camelot Village and we will head out on the trails from there. We can have one intermediate ride at a relaxed pace, and one advanced ride that will cover more distance and have more climbing. Please plan on around 1.5-3 hours. If there are any kids, we’ll start at the pump track at Stark Street and do a few easy trails around the hospital.

This is a great time to meet other riders from around Southwestern Vermont and network.

Sunday Ride

When: Sunday, September 15 at 2 p.m.

Where: Barrows House Inn & Restaurant, 3156 Vermont 30, Dorset, VT 05251


Plan to join Northshire Area Trail Systems up in the Northshire of Southwestern Vermont on Sunday! This guided ride will take bikers on two options based on group interest.

  1. A difficult 11-mile ride with 1,200 feet of climbing. 50% dirt road in Dorset Hollow, 50% long out and back hand-built singletrack climb and descent.
  2. A moderate to difficult tour through a network of hand-built singletrack with multiple options to customize distance and climbing based on group interest.

Here’s a self-guided option:  The Gravel Grinder self-guided ride from Barrows House, around the Dorset Hollow and back is about 6 miles long and on rolling terrain.

Post-ride, guests can opt for beers and burgers at the Barrows House.

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.

Bennington Area Trail System


BATS was founded by a group of local bikers, runners, and hikers that advocate for multi-use singletrack trails for the enjoyment of area residents and visitors alike.

Merck Forest & Farmland Center


MFFC is a nonprofit educational organization on a mission to inspire curiosity, love and responsibility toward our natural and working lands.

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, 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


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


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.

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.