The Shires of Vermont

2020 Stay to Stay Ski Weekend

February 21-24, 2020

Welcome to Vermont's Stay to Stay Weekend program! This is a special weekend as we offer a "Ski to Stay" Weekend as part of this popular program for potential Vermonters. If you're a skier or boarder or do anything with winter and snow, we want you here!

This is an exploratory vacation weekend for people who are interested in moving to Vermont (especially for our awesome winters!). The 3-day weekend connects guests to employers, community leaders, entrepreneurs, and potential neighbors in local communities around Vermont.

This specific location is in The Shires of Vermont in Southwestern Vermont (less than 4 hours from NYC, Boston and Montreal). We will "roll out the red carpet" and introduce our Stayers to the beautiful Shires region. Work with a dedicated team at the local chamber to get one-on-one connections to employers, schools, start-ups, and housing opportunities. Sign up for this location and receive free lift tickets to Bromley Mountain!

After your Saturday ride on Bromley, join the Bromley team and the local Stay To Stay team as they host a meet and greet at the base lodge of Bromley Mountain starting at 5:30 p.m. Light cocktails and appetizers will be served. Come meet with local townspeople and community leaders as well to get a sense of the region.

As part of your Ski to Stay Weekend, join the team again on Monday morning at 8 a.m. at the Manchester Welcome Center for coffee, cider, donuts, cheese and more (18 Depot Street, Manchester Center)! We want to get you up and at 'em before you go to check out our employment, housing, and educational opportunities throughout the Northshire region. Join us for an hour of our signature program, Coffee & Conversations. Meet with locals and start the morning off right! 

Did You Know?

  • In 1856, Charles F. Orvis opened a store dedicated to fly-fishing and related accessories, now known as the Orvis company, which is the oldest operating mail order business in America.
  • The snowboard was invented in 1977 by Jake Burton Carpenter in his Manchester garage.


Welcome Reception

After your Saturday ride on Bromley, join the Bromley team and the local Stay To Stay team as they host a meet and greet at the base lodge of Bromley Mountain starting at 5:30 p.m. Light cocktails and appetizers will be served. Come meet with local townspeople and community leaders as well to get a sense of the region.

Bromley Mountain Resort
Physical Address for GPS Devices:
• 3984 Vermont Route 11, Peru, VT 05152
• or 144 Bromley Lodge Rd., Peru, VT 05152
(802) 824-5522

Other Weekend Activities

Experience Downtown Bennington's many shops, restaurants, and sidewalk cafés. Enjoy a vibrant cultural scene in the Arts District with live theater, art galleries, museums, and Vermont’s largest downtown Wi-Fi network. Walk along the Riverwalk, stop by the robust farmers market and stock up at Vermont’s largest arts supply store.

Manchester is a quaint mountain town with many activities to choose from: fly-fishing in the Battenkill, skiing at nearby Stratton Mountain Resort and Bromley Mountain Resort, browsing in the independent, family-owned Northshire Bookstore, snagging bargains at the outlets stores, visiting downtown merchants, strolling along the marble sidewalks in historic Manchester village, and the list goes on. If you’re simply wanting some peace and quiet, The Spa at the Equinox or the Manchester Riverwalk are two guaranteed ways to help you rejuvenate.

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. 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. Address for the employer reception: Manchester Welcome Center, 18 Depot Street, Manchester Center, Vermont 05255. You can also sign up to meet with a local realtor who can show you potential housing options, visit a co-working or maker space, or visit a child care center. Please RSVP so we can get an accurate number of attendees.


Monday, from 10 a.m.–1 p.m. The employer industry sectors offered include:

Start up
Nonprofit services

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


Paul Carroccio
TPW Real Estate
4903 Main Street
Manchester, VT 05255

Dave Citron
REMAX Four Seasons
2897 Depot Street
Manchester Center, VT 05255

Co-working/Maker Space

Monday, from 10 a.m.–1 p.m. at the The Lightning Jar
194 North Street
Bennington, VT 05201


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

The Bennington Area Chamber of Commerce logo.


The Bennington Area Chamber of Commerce promotes, leads, and advocates a unified effort, on behalf of its members, to maintain and improve a healthy business climate and rewarding quality of life.

Bromley Mountain Ski Resort logo.
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 skier takes a run down the terrain park at Mount Snow Resort.

Southeastern Vermont

Mount Snow
February 21-24, 2020

Meet with representatives from the Deerfield Valley and Brattleboro areas at Mount Snow Resort. Mount Snow is just 2.5 hours from Boston and 4 hours from New York City, making it one of the most accessible ski mountains from southern metropolitan areas.

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!

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.