Support Vermont Communities


Southeastern Vermont

2020 Stay to Stay Weekends

February 21-24, May 1-3, and October 2-5, 2020

We'll Still be Here

Right now, it's much more important for everyone to stay home and stay safe. Due to the COVID-19 outbreak, we are postponing indefinitely all Stay to Stay Weekends. We'll announce future dates as soon as we can.

Even though you can't take an exploratory vacation right now, you can still take in life in Vermont virtually, watch our Stay to Stay video series, and follow Vermont Tourism on Facebook, Twitter and Instagram.

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 have 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 daytrip to Boston or a weekend trip to New York or Montreal—and we do!

Through Stay to Stay Weekends you can sample the region’s offerings. Southeastern Vermont 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.
  • Southeastern Vermont is a cultural hub featuring 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, the New England Center for Circus Arts.
  • 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, and kayak all summer long!
  • Brattleboro has 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.


Health Care Employer Connections

Date: May 1, 2020, 9-10am, 11am-12pm, 1-2pm, 3-4pm
Location: Brattleboro Memorial Hospital, Health Care and Rehab Services (HCRS), Grace Cottage Hospital, and the Brattleboro Retreat.

The May Stay to Stay Weekend will have a special focus on healthcare jobs and careers. If you are a healthcare professional, don’t miss this opportunity to meet employers who have openings for all levels of healthcare related jobs.

On Friday during the day, you will have a number of employer information sessions to choose from. Visit Brattleboro Memorial Hospital, Health Care and Rehab Services (HCRS), Grace Cottage Hospital, and the Brattleboro Retreat. Meet with their HR staff, hear from current employees, and get a tour of the facilities. After you register for the weekend, you'll receive a registration form in an email from the Stay to Stay hosts, where you will sign up for specific employers at specific times.

Welcome & Networking Reception

Date: May 1, 2020 at 5 pm
Location: Downtown Brattleboro, location TBD

Join local community members and the other Stay to Stay guests at a welcome and networking reception in the heart of downtown Brattleboro. Hear from locals about what it is like to live and work in Southeastern Vermont. Gather suggestions on places to see, shows to attend, and food to eat from the people that know the ins-and-outs of these communities.

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 Friday reception 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

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? These participating realtors 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.

Due to the COVID-19 outbreak, we are postponing indefinitely all Stay to Stay Weekends. We'll announce future dates as soon as we can.

Brattleboro Memorial Hospital, Exceptional Care for Our Community

Brattleboro Memorial Hospital

Founded in 1904, Brattleboro Memorial Hospital (BMH) is a licensed, 61-bed, not-for-profit community hospital located in southeastern Vermont, serving a rural population of about 55,000 people in 22 towns in Vermont, New Hampshire and Massachusetts. The BMH medical staff includes board-certified providers in primary care and many other specialties, with a shared mission of providing exceptional health care delivered with compassion and respect. 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 patients’ 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! #lovebrattleborovt

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.