Southeastern Vermont

2020 Stay to Stay Weekend

February 21-24, May 1-4, and October 2-5, 2020

Whether you are looking for outdoor recreation, arts and culture, or small-town vibes, we've got it all here in Southeastern Vermont. You can live next to a mountain, ski before work and still leave an easy commute to regional employment hubs. You can live in town and walk to work, enjoy entertainment and local food at your doorstep, and still get away deep into nature any day after work. This is also one of the most accessible regions of Vermont in relation to the rest of New England. We are part of a “tri-state” region with New Hampshire a stone’s throw away, and Massachusetts just a few miles south of Brattleboro. From here it’s easy to enjoy a day-trip to Boston, a weekend trip to New York or Montreal and we do!

Through Stay to Stay weekends you can sample the region’s offerings. Stay to Stay Weekends take place in Brattleboro, the first exit in Vermont for travelers heading north on I-91, and in Wilmington/Dover in the Deerfield Valley region of the Green Mountains.

Did you Know?

  • Brattleboro is the one and only town in the world named Brattleboro.
  • This region is a cultural hub including music every night in Brattleboro, world-class Jazz at the Vermont Jazz Center, classical music all summer at the Marlboro Music Festival, and one of the world’s leading circus arts training facilities at NECCA.
  • There are 20 ski areas within a 90 minute drive in Southeastern Vermont, but there is also water everywhere and we love to swim, fish, canoe or kayak all summer long!
  • Brattleboro has retained a disproportionately large number of bookstores. That fealty to the printed page is consistent with the town’s impressive literary tradition including publishers as well as writers. A list of big-name authors who have lived in or frequented Brattleboro begins with Rudyard Kipling and includes Robert Frost, Sinclair Lewis, Pearl Buck, Grace Paley and Jamaica Kincaid.


Welcome Reception

The Welcome Reception takes place on Friday at 5 p.m. Gather in the quaint and eclectic downtown Brattleboro with Stay to Stay guests, community members, and employers and converse about the joys and benefits of living in Southeastern Vermont.

Weekend Activities

Explore the one and only Brattleboro. Experience the simple 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. Brattleboro’s neighborhoods come in all shapes and sizes. Wind your way through 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 Whetstone Station Restaurant and Brewery, Hermit Thrush Brewery, or at Saxtons River Distillery.

Or consider taking a drive and exploring the many wonderful towns in the Deerfield Valley—and find lots of family-friendly things to do. Take some time to relax at one of the area's many spas or salons. Take in a movie at the newly renovated cinema. Unique to New England, nine pin bowling can be found right here in the Valley at North Star Bowl along with arcade games and indoor putt-putt.

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. Also, 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. You can also sign up to meet with a local realtor who can show you potential housing options.


If you are staying through Monday, use this time to meet with a realtor and explore surrounding towns!

Do you want to live walking distance to downtown Brattleboro? Are you looking for some acres at the base of a mountain? Either realtor can help you find your new home!

Meg Streeter Real Estate - Meg Streeter

Berkley & Veller Greenwood Country Realtors - Maria Diran


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

Brattleboro Memorial Hospital, Exceptional Care for Our Community

Brattleboro Memorial Hospital

The Brattleboro Memorial Hospital Health System includes the BMH Medical Group, a multispecialty group practice of primary care and specialty care physicians, nurse practitioners, and physician assistants.

Brattleboro Retreat, Mental Health and Addiction Care

Brattleboro Retreat

At the Brattleboro Retreat we believe in providing effective, compassionate mental health and addiction care that is based on scientific evidence and centered on you. Here on our safe, restorative Vermont campus, our patient’s well being motivates us while their courage inspires us.

Grace Cottage Family Health & Hospital

Grace Cottage Hospital

At Grace Cottage, we go beyond patient care. Located in Townshend, just 25 minutes northeast of Brattleboro, we serve the healthcare needs of our community; to promote wellness, relieve suffering, and restore health.

Health Care & Rehabilitation Services of Southeastern Vermont

Health Care & Rehabilitation Services of Southeastern Vermont

HCRS’s integrated services help individuals and families in our communities to live happy and successful lives.

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!

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.

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.


Southeastern Vermont offers many different lodging experiences, from commercial-sized hotels to the quaint bed and breakfasts. You may find your home away from home on the list of lodging available in the area.

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.


A slalom skier takes a run at Killington Mountain Resort.


Killington Grand Resort
March 13-15, 2020

Meet employers and residents from the Rutland area at Killington
Grand Resort, the second highest peak in Vermont at 4,241 feet. Killington is known as the “Beast of the East” and has welcomed over 39K spectators and athletes from 20 different countries participating in the
FIS Alpine Ski World Cup.