Real Rutland Weekend Getaway | September 22-25th 2022

Are you considering moving to Vermont? This Weekend Getaway could be your opportunity to explore Rutland County during the breathtaking fall foliage season. Enjoy a free stay at the Killington Grand Hotel and vouchers to local restaurants. Choose between guided or solo explorations through our mountains and downtowns, talk with a realtor, visit area schools, and meet locals who also fell in love with this unique part of Vermont. This weekend is for single people, couples, and families who are serious about making The Green Mountain State their new home.

You must interview with one of our concierge program coordinators for eligibility.

Winners announced Aug 3, 2022.

Congratulations to the following households:

Amanda C. of Illinois, Jiri B. of North Carolina, Katherine T. of New York, Katie C. of Texas, and Michelle C. of California


DAY 1 - Thursday, arrival by 5:00 pm:

  • Free rental car is available for each household.
  • Contest winners will be greeted by a concierge upon arrival in Killington
  • Contest winners will receive gift cards to local restaurants for all meals
  • Guests will receive free accommodations at the Killington Grand Hotel and Resort
  • Meet & Greet dinner with local hosts on the first evening from 5:30 – 7:00 p.m.

DAY 2 - Friday, Guided or self-guided activities which include:

  • Hiking
  • Mountain biking
  • Kayaking
  • Gondola ride to the top of Killington
  • Buffet style lunch at a local restaurant
  • Visit to downtown Rutland and the MINT Makerspace
  • Dinner on your own (gift certificates provided)
  • County-Wide Scavenger Hunt with a $200 gift basket from Baird Farm
  • Show at the Paramount Theatre (pending schedule)

DAY 3 - Saturday, Options for guided or self-guided tours with lunch on your own (gift certificates provided):

  • The Umbrella Art and Specialty Shop Tour with stops at the Red Clover Ale, Chaffee Art Center, Sparkle Barn, Carving Studio and Sculpture Center, Brandon Artists Guild, Vermont Folk Gallery, Chaffee Art Center, and Downtown Rutland mural walk.
  • County-Wide Scavenger Hunt with a $200 gift basket from Baird Farm
  • Killington Brewfest at Pico Mountain 1 – 4 p.m.
  • Covered Bridge Discovery Tour
  • Early Buffet Dinner at Southside Steakhouse.
  • Show at the Paramount Theatre (pending schedule)

DAY 4 - Sunday. Goodbye Breakfast at Sugar & Spice 10:00am – CEDRR Staff



The Vermont Weekend Getaway Contest is now Closed.

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Things to do, places to stay, quality of life. Adventure outdoors, micro- breweries, farmers markets and quaint Bed & Breakfasts await! Download our curated list of recommendations.

Contact our concierge to arrange your visit to Rutland County Vermont for an exploratory weekend of fun and adventure. Meet with locals, employers, and realtors in the area, all while hitting the slopes.

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