Southeastern Vermont

2019 Stay to Stay Weekends

October 25–28, 2019

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 the 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. 

The one and only Brattleboro dances on the edge of Vermont — an urban arts oasis located in the foothills, where you can find cows on parade, the Metropolitan Opera and Vermont Jazz Center, and world-class aerial circus arts all comfortably side-by-side in a vibrant, historic downtown. Overlooking the Connecticut River, Main Street is lined with buildings that house galleries, restaurants, shops, breweries, and 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. Many of the region’s jobs are located here, an easy commute from nearby communities. Many choose “live-work” convenience of living here, and the ability to walk or bike to work in town.  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.” 

Just west of Brattleboro, nestled in the Green Mountains, you will find endless trails great for hiking and exploring in Wilmington/Dover. While known as a winter wonderland with outstanding ski resorts, we absolutely shine in the summertime. Rent a bike, kayak or paddle board to really get to know the valley.  With great shopping and galleries, these towns provide a doorway to local talent and unique treasures. Foodies take heart! It’s also home to an amazing amount of farm to table businesses and restaurants that will provide you with innovative, delicious and fresh local fare. Many people choose the wonderful lifestyle, small schools and tight-knit communities of the valley, where they can take a run on the slopes before heading to work and enjoy a beautiful mountain top sunset view every evening from their own backyard.  


Welcome Reception

The Welcome Reception takes place at 5 p.m. at The Lounge.

4 High Street
Brattleboro, VT 05301
(802) 254-4141

Weekend Activities

Saturday and Sunday are unscheduled so that guests can explore the community and its many attractions.

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.

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, or to visit a co-working or maker space.

Coffee & Conversations

Monday, at 9 a.m. at the Brattleboro Food Co-op
2 Main Street
Brattleboro, VT 05301

Employer Industry Sectors

Meet with employers during the Monday morning Coffee and Conversations from 9-10:30 a.m. at the Brattleboro Food Co-op. 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 and Conversations on Monday morning.


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

Monday, at 10:30 a.m. at Brattleboro Area Realty
163 High Street
Brattleboro, VT 05301

Incubator Space

Monday, at 10:30 a.m. at The Cotton Mill,
74 Cotton Mill Hill
Brattleboro, VT 05301


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

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.


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.

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.

The Equinox in Manchester, Vermont.


October 25–28

Bennington and Manchester are located in the beautiful region between the Taconic Range and the Green Mountains.