Real Rutland Weekend Getaway | October 12-15, 2023

Thank you to all who entered and interviewed with a Real Rutland Concierge. Our winners have been selected and are listed below. Please connect with our Real Rutland Concierge Coordinator, Karly Haven, if you are still interested in learning more about moving to Rutland County, Vermont.

Thomas G. from Texas, Matthew B. from Texas, Erik A. from Connecticut, and Daniel C. from Ohio. 

Connect with Real Rutland Concierge Coordinator, Karly Haven here.

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

  • A free rental car is available for each household
  • Contest winners will be greeted by a concierge in Killington
  • Contest winners will receive money intended for use at local restaurants for all meals not scheduled
  • 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
  • Visit Downtown Rutland and the MINT Makerspace
  • Breakfast, lunch, and dinner on your own (money 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

  • 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
  • Covered Bridge Discovery Tour
  • Breakfast and lunch on your own (money provided)
  • Dinner at Southside Steakhouse.
  • Show at the Paramount Theatre (pending schedule)

DAY 4 - Sunday, Goodbye Breakfast at Sugar & Spice

  • 10:00 a.m. breakfast with the Chamber & Economic Development of the Rutland Region staff before everyone begins their travel



The Real Rutland Fall 2023 Weekend Getaway entry period has ended. We will announce the winners on August 29, 2023. If you are still interested in Rutland County or thinking about relocating to Vermont, please connect with us here, https://realrutland.com/concierge/

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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.

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