REAL RUTLAND VERMONT WEEKEND GETAWAY | MARCH 20-23, 2025
ARE YOU CONSIDERING RELOCATING TO VERMONT? THIS WEEKEND GETAWAY COULD BE YOUR OPPORTUNITY TO EXPLORE RUTLAND COUNTY DURING THE SKI AND MAPLE SEASONS WITH A FOCUS ON MOVING HERE.
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.
THE GIVEAWAY OPENS ON JANUARY 6, 2025, AND INTERVIEWS BEGIN ON JANUARY 29, 2025.
YOU MUST INTERVIEW WITH ONE OF OUR CONCIERGE PROGRAM COORDINATORS BY FEBRUARY 12, 2025, FOR ELIGIBILITY.
DAY 1 - Thursday, arrival by 5:00 pm:
- Money for a rental car is available for each household
- Contest winners will be greeted by a concierge volunteer 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. Location TBD
DAY 2 - Friday, Guided or self-guided activities which include:
- Skiing/Snowboarding
- School visits
- Breakfast, lunch, and dinner on your own (money provided)
- The Umbrella Art and Specialty Shop Tour
- County-Wide Scavenger Hunt for a $200 gift basket from Baird Farm
- Show at the Paramount Theatre (pending schedule)
DAY 3 - Saturday, Options for guided or self-guided tours
- Vermont Maple Open House Weekend
- Skiing/Snowboarding
- Visit Downtown Rutland
- County-Wide Scavenger Hunt for a $200 gift basket from Baird Farm
- Covered Bridge Discovery Tour
- Breakfast, lunch, and dinner on your own (money provided)
- Show at the Paramount Theatre (pending schedule)
DAY 4 - Sunday, Goodbye Breakfast at Sugar & Spice
- 9:00 a.m. breakfast with the Chamber & Economic Development of the Rutland Region staff before everyone begins their travel
The Real Rutland Vermont 2025 Weekend Getaway entry period has ended. We will announce the winners on February 17, 2025. 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
Mount Holly, VT Minutes From Okemo Mount Holly, Vermont, is the hometown of snowboarder Hannah Teter, who...
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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