OCTOBER 19-22, 2018

The one and only Brattleboro dances on the edge of Vermont — an urban arts oasis nestled in the foothills, where you can find cows on parade, the Metropolitan Opera, and world-class aerial circus arts all living comfortably in a vibrant, historic downtown.

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

Businesses small and large, from manufacturing, health care, and education to the arts, make Brattleboro the economic hub of southeastern Vermont. And with easy access to major cities like New York and Boston, you can get here via trains, planes and automobiles! It’s no wonder Fodor’s named Brattleboro “One of the Best Small Towns in America.”

Did You Know?

  • The first civil union joining a same-sex couple in the United State was performed in Brattleboro on July 1, 2000.
  • Brattleboro is home to New England’s only Olympic-size ski jump. For 95 years, world-class jumpers have flocked to Brattleboro to take part in the annual Harris Hill Ski Jump Competition.
  • The first U.S. edition of the Harry Potter series was printed in Brattleboro in 1997.


Friday Evening

Welcome Reception will take place at 5 p.m. at The Lounge
4 High Street
Brattleboro, VT 05301
(802) 254-4141

Saturday & Sunday

These are your days for exploring.

Experience the just plain goodness of small-town living, friendly neighbors, an exemplary library, lots of well-kept and stocked parks and play areas, and a great school system. Our neighborhoods come in all shapes and sizes. Wind your way through our many side streets, and you’ll soon discover Brattleboro’s hidden gems. Catch a movie or concert at the Latchis Theatre, view the ever-changing exhibits at the Brattleboro Museum and Art Center. Enjoy a tasting at Whetsone Station Restaurant and Brewery, Hermit Thrush Brewery, or at Saxtons River Distillery. There are plenty of forested trails that offer hiking, biking, skiing, and snowshoeing, or you can swim in one of the many rivers and ponds.

Monday Morning

Pick one of the following places to visit Monday morning. This is your opportunity to meet with a local employer, have a realtor show you potential housing options, or visit a co-maker space.


Monday, at 10 a.m. at Brattleboro Retreat
1 Anna Marsh Lane
Brattleboro, VT 05301

Monday, at 10 a.m. at Green Mountain Creamery
3 Omega Drive
Brattleboro, VT 05302

Monday, at 10 a.m. at Mondo Mediaworks
11 University Way, Suite #4
Brattleboro, VT 05301

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


Monday, at 10 a.m. at Meg Streeter Real Estate
6 S. Main Street
Wilmington, VT 05363

Monday, at 10 a.m. at Brattleboro Area Realty
163 High Street
Brattleboro, VT 05301


Monday, at 10 a.m. at The Cotton Mill,
74 Cotton Mill Hill
Brattleboro, VT 05301

If you plan to attend the upcoming Stay to Stay Weekend in October, 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 October weekend is October 5th.

The Downtown Brattleboro Alliance logo.

Downtown Brattleboro Alliance

We are the One and Only Brattleboro, a small Vermont town with a thriving downtown serving the artistic, social, and economic community for miles around. We regularly make the “Best small town” lists of many publications, come for a visit and see why!

The Brattleboro Area Chamber of Commerce logo.


The Chamber is proud to be one of the leading business and community organizations in Windham County. The Chamber’s mission is to promote and enhance a thriving business community. They work with their 400-plus member businesses and organizations to articulate the region’s needs and find creative solutions.

Brattleboro Development Credit Corporation logo.


The Brattleboro Development Credit Corporation (BDCC) is dedicated to assisting start-up companies, growing companies, and global businesses alike, in order to support continued success stories in the region. Their primary objective is to create and retain a flourishing business community that supports vibrant fiscal activity and improves the quality of life of all its residents.


1868 Crosby House Bed & Breakfast
(802) 257-7145
175 Western Avenue, Brattleboro, VT 05301

Inn on Putney Road
(802) 536-4780
192 Putney Road, Brattleboro, VT 05301

Holiday Inn Express Hotel & Suites
(802) 257-2400
100 Chickering Drive, Brattleboro, VT 05301

Latchis Hotel
(802) 254-6300
50 Main Street, Brattleboro, VT 05301

Landmark Trust USA
(802) 254-6868
707 Kipling Road, Dummerston, VT 05301

Questions About Stay to Stay?

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

What is the cost of the Stay to Stay Weekend? 

The cost will vary depending on which accommodation you select. To qualify for the program, guests book their own 3-night stay at a commercial lodging property to gain access to the networking receptions, employer visits, and connections with community leaders who can facilitate your relocation to Vermont.

Can I sign up for the Stay to Stay weekend if I am not a U.S. resident?

The Stay to Stay Weekend is not an immigration or work visa program. Citizens of foreign countries interested in traveling, living or working in Vermont need to secure the appropriate visa from the U.S. State Department. You can find more information here

I read about Vermont paying people $10,000 to move there. How can I apply? 

The Stay to Stay Weekend is not part of recently announced remote worker grant program that goes into effect January 1, 2019. You can find details on that program at ThinkVermont.com or email info@thinkvermont.com

If you have more questions than we covered here, please click on "Contact Us" below to send us an email.


Church Street Marketplace in Burlington, Vermont.


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.

Mother and son chat on the sidewalk at the Equinox.


A popular travel destination since the 1800s, Manchester is steeped in history. You can visit a nationally recognized historic site and museum or join a guided tour and soak up the story of Vermont firsthand.

Downtown Rutland, Vermont.


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.