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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Visit & Stay
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.
Visit the Towns of Rutland County and Find Out What Makes Each One Distinct
Killington
town of Killington Mountain Access Killington is home to both Killington Peak and Pico Peak, and has...
Castleton
Town Of Castleton Friendly and Picturesque Castleton is best known as home to Castleton University, a public...
Downtown Rutland
CITY OF RUTLAND Historic Downtown Rutland's historic downtown is the seat of Rutland County and the heart...
Pittsford
TOWN OF Pittsford Sunshine Village Pittsford was first settled in 1769, and still hosts archaeological remains of...
Clarendon
TOWN OF Clarendon Clarendon Gorge Just south of Rutland City, Clarendon, Vermont, is home to the Rutland...
Mendon
Mendon Make It Homebase Mendon is situated on the Long Trail at the base of Killington Mountain,...
Ira
Ira, VT Perserving History The people of Ira are dedicated to preserving the rich history of their...
Hubbardton
TOWN OF Hubbardton Home of The Battle of Hubbardton Hubbardton is best known for the Battle of...
Wallingford
TOWN OF Wallingford Green Mountain National Forest With more than half of its land area in the...
West Rutland
TOWN OF West Rutland Land of Marble Chartered in 1761, West Rutland found its place on the...
Wells
Wells, VT Lake St. Catherine and Little Lake Swimmers and kayakers, rejoice. Wells, Vermont is lucky to...
Poultney
TOWN OF Poultney Home of the Good Life Poultney is located on the New York-Vermont border and...
Mount Holly
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Fair Haven
TOWN OF Fair Haven Vermont's Western Gateway The town of Fair Haven is widely regarded as the...
Tinmouth
Tinmouth, VT Remote and Wild Tinmouth lies 25 minutes south of Rutland, where a small population enjoys...
Sudbury
Sudbury, VT Where Farmland and Mountains Mingle In the northwestern corner of Rutland County sits Sudbury, Vermont,...
Pawlet
TOWN OF Pawlet Taconic Mountain Town Although Vermont is best known for the Green Mountains, the Taconic...
Shrewsbury
town of Shrewsbury Nature Lover's Dream There's just something about Shrewsbury when it comes to love and...
Brandon
TOWN OF Brandon Vermont's 'Art and Soul' Brandon is known as the 'Art and Soul' Village of...
Chittenden
TOWN OF Chittenden Unbroken Forest Chittenden is Vermont's largest town by area, chartered in 1780 and named...
Pittsfield
Pittsfield, VT Mountains and Maple Syrup Pittsfield makes good use of its mountainous terrain and New England...
Benson
TOWN OF Benson Rural Vermont Charm Bounded on the west by Lake Champlain - the eighth largest...
Rutland Town
Rutland Town Natural Wonder & Renowned Hospitality Rutland is situated between two mountain ranges, the Green Mountains...
#REALRUTLAND Life in Rutland County Vermont
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