2020 Stay to Stay Ski Weekend

March 13-15, 2020

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.

Lifestyle freedom flourishes here — our residents can easily claim their very own home sweet home, enjoy a range of year-round outdoor activities, and raise families among a network of great K–12 and college-level schools. Whether you’re looking to take the next step in your career or launch that dream business, Rutland County is the perfect place to put down roots for young and seasoned professionals alike.

Did You Know?

  • Rutland is the solar capital of New England, with more solar power installed per capita than any other city in New England.
  • Rutland County has the largest four-season farmers market in the entire state.
  • John Deere, inventor of the steel plow, was born and raised on Main Street in Rutland in the early 1800s.


Welcome Reception

The Welcome Reception will take place from 6:30–8 p.m. on Saturday evening at the Killington Grand Resort.

4763 Killington Road
Killington, VT 05751
(800) 734-9435

Weekend Activities

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

Enjoy the many amenities Killington has to offer and spend the day skiing and riding on its dozens of amazing trails. Relax in the spa, ride the Beast Mountain Coaster, take a snowshoe tour, or try all the great winter activities available for families and couples.

You can also come down off the mountain to explore Rutland. With dozens of shops and restaurants, as well as a world-class performing arts venue, downtown Rutland is the perfect destination to shop, eat, and be entertained. Visit one of the town's many unique shops as you make your way to the acclaimed Vermont Farmers Market in Depot Park. Grab a bite and maybe a local brew in one of many independently owned localvore restaurants before taking in a show at the brilliantly restored 1912 Paramount Theatre.

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

Monday at 9 a.m. at an employer from the following industry sectors offered on this weekend:
Health Care

Please note if you choose to meet with an employer, the local Chamber will request a copy of your resume.


Monday at 11 a.m. at Sotheby’s Four Seasons International Realty
85 N. Main Street
Rutland, VT 05201

Co-working/Maker Space

Monday from 10 a.m.–12 p.m. at The Mint – Rutland’s Makerspace,
112 Quality Lane
Rutland, VT 05701


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

The Rutland Chamber of Commerce logo.


The Rutland Region Chamber of Commerce is a membership organization whose purpose is to connect member business organizations with community and visitors, promoting the region as a great place to live, work, and play.

Rutland Young Professionals logo.


An all-volunteer, all-inclusive organization focused on creating a vibrant Rutland area and promoting that area to young professionals near and far. Founded in July of 2013 by a core group of energetic folks seeking a way to connect with other people, jobs, volunteer and mentor opportunities, professional development, and fun.

Killington Ski Resort logo.


Rutland offers an array of different lodging experiences, from commercial-sized hotels to quaint bed and breakfasts. You may find your home away from home by exploring lodging options available in the Rutland region, Brandon region, or Killington region.

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.


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.

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 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.