Southeastern Vermont

2020 Stay to Stay Ski Weekend

February 21-24, 2020

Whether you are looking for outdoor recreation, arts and culture, or small-town vibes, we've got it all here in Southeastern Vermont, one of the most accessible regions of the state. 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.


Welcome Reception

The Welcome Reception takes place on Friday at 5 p.m. in the Carinthia Lodge at Mount Snow Resort. Gather in the warm lodge with skiers, Stay to Stay guests, and community members and converse about the joys and benefits of living in the Deerfield Valley.

39 Mount Snow Road
West Dover, Vermont

Weekend Activities

Friday arrivals will enjoy our Welcome Reception as well as access to special discount ski passes (available for Friday arrivals only). As a special opportunity for our Stay to Stay guests, you will receive discount ski passes to make the most out of your trip - just send an email with the names and ages of those interested to slang@brattleborodevelopment.com or reserve yours here. Saturday and Sunday are unscheduled so that guests can hit the slopes and experience the area and its many attractions.

Explore 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.  

Or explore neighboring Brattleboro, just 45 minutes from the mountain. 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

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.

Employer Industry Sectors

Meet with employers during the Monday morning Coffee & Conversations from 9-10:30 a.m. at the The Village Roost. Participating employer industry sectors offered include:

Tech and Finance
Health Care
Public Safety/Government
Manufacturing Food & Beverage

Please note if you choose to meet with employers, the local Development Corp. will request a copy of your resume. This will be shared with employers who will be attending the Coffee & Conversations on Monday morning.

Coffee & Conversations

Monday at 9 a.m. at The Village Roost 
20 West Main Street
Wilmington, Vermont 05363 


Monday, at 10:30 a.m. at Meg Streeter Real Estate
6 South Main Street
Wilmington, VT 05363


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

Southern Vermont Deerfield Valley Logo

Southern Vermont Deerfield Valley

Southern Vermont's Deerfield Valley is a community composed of ten towns. Dover-Home of Mount Snow Resort, Wilmington-Historic Shopping District, Wardsboro-Outdoor adventures, Marlboro-Marlboro college and Music Festival, Searsburg, Stamford, Readsboro-with Readsboro Gorge. Whitingham, Jacksonville, and Halifax host our farms, artisans, and our working community.

Mount Snow logo.
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.


Brattleboro 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.


Jay Peak


Jay Peak
December 13-16, 2019

Experience the exceptional work/life balance that you can find in Vermont's Northeast Kingdom, as well as the most snow in the East at Jay Peak Resort. Once you’ve conquered the slopes, explore the scenic countryside in this close-knit community close to the Canadian border, or beat the cold in the Resort's indoor water park!

Two skiers ride the chairlift, at Bromley Mountain Resort, for their next run.

The Shires of Vermont

Bromley Mountain
February 21-24, 2020

Residents and employers from the Bennington and Manchester area—the Shires of Vermont-- will greet you at Bromley Mountain Resort. Bromley is the only major ski resort in New England with a southern exposure, providing skiers and riders with full sunshine on all 47 trails.

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.