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Saturday, December 3, 2022


Join Highland County, Virginia during the holiday season each year on the first Saturday in December. Slow your pace, and enjoy the sights, sounds, and tastes of this special time!

Thank you to everyone who made our Saturday, December 3, 2022 Wintertide a success!

*** Below, you'll find information about 2022.  Please check closer to the 2023 event for updates ***

The Highland Center
61 Highland Center Drive, Monterey
10 am - 5 pm Kids' crafts, Wintertide Market with local vendors.
Interested in being a vendor? Click here!
10 am - 2 pm Susanna's Confections is open for tasty treats (including free hot chocolate and a cookie for kids!)
11 am - 1 pm Visit with Santa
3 pm  Clogging performance by The Little Switzerland Cloggers

Special thanks to Blue Grass Valley Bank for sponsoring the annual Christmas tree!

Decorations for the tree will be provided by Highland Children's House.

Big Fish Cider Co. 
59 Spruce Street, Monterey
2 - 7 pm
Swing by the Big Fish Cider tasting room and try one of their award winning ciders, made with locally grown and harvested apples. Enjoy free hot mulled (nonalcoholic) cider as a merry taste of the season. Plus, get $5 off a 3 bottle purchase by showing your 2022 Maple Festival Keychain as part of Sweet Deal Days!

Blue Grass Valley Bank Holiday Coloring Contest
132 E. Main Street, Monterey or 2583 Blue Grass Valley Road, Blue Grass
Join the Blue Grass Valley Bank in a Holiday Coloring Contest!  Age groups: 4 & under, 5-10 yrs, 11-15 yrs, or 16+.  Pictures can be picked up at any Blue Grass Valley Bank location between November 28 - December 16, 2022. Each age group has its own picture, only one entry per participant. Entries for contestants under the age of 18 must leave a parent’s or guardian’s contact information. All completed entries must be received by 6 pm Friday, December 16.  Pictures must be colored with crayons, colored pencils, or both!  Markers will be disqualified.  Each entry will be displayed without the participant's name at the location it is turned in until the end of the contest. Please write the participant's name on the back in pencil. BGVB employees will choose the top three for each group. Community voting will be available December 23 - 30.  Entries will be judged on creativity, coloring skill, and overall appeal.  The winners will be announced on January 3, 2022 and will receive a $15 cash prize.
Plus, The Grinch will be on site at The Blue Grass Valley Bank on December 23 handing out cookies!  Stop by for a visit!

The Curly Maple
174 West Main Street, Monterey
10 am - 7 pm
Enjoy winter-inspired lunch and dinner faire, holiday inventory, local goods, and more!
Taste the following dinner menu highlights of pub style food between 4:30 and 7 pm with carry out options:
- Fried pickles with zesty ranch
- Homemade boneless wings (Buffalo or Asian Plum) with homemade ranch and celery
- Jumbo lump crab cake sandwich on grilled brioche with homemade remoulade and beer battered french fries
- Beulah Springs loaded cheeseburger with beer battered french fries
- Pulled chicken avocado club with beer battered french fries 

High's Restaurant
73 West Main Street, Monterey
11 am - 8 pm
Enjoy delicious food from a local staple, including an Inch-thick Ribeye Steak of 12 - 16 Ounces with 2 Sides on Sale for $24.95 (Regularly $34.95).  Extend your Wintertide by taking advantage of this steak dinner special a day earlier on Friday, December 2 from 11 am - 8 pm or a day later on Sunday, December 4 from 11 am - 7 pm, too!  Plus, get 10% off the meal purchase and High's Official Merchandise by showing your 2022 Maple Festival Keychain between November 26 and December 3 as part of Sweet Deal Days!

Highland County Recreation Commission Holiday Lights Contest
A Holiday Lights Contest is open to all Highland County residents and businesses, and what better way to start than during Wintertide? Award categories include: Clark Griswold, Classic Holiday Elegance, Winter Wonderland, and Gingerbread House. Enter by emailing your name address, phone number, email address, and category entry to by December 15. Entries will be judged from December 16-18 and winners will be announced on December 21.  Get full details by clicking here!


Highland Inn Open House from the Blue Grass Resource Center
68 W. Main Street, Monterey
11 am - 3 pm
Enjoy refreshments as you learn about the historic Highland Inn renovation project from the current owners.

Laurel Fork Sapsuckers
10677 Mountain Turnpike, Hightown
10:30 am - 4 pm
Swing by, enjoy light refreshments, and pick up some delicious syrup and other gifts for friends and family.  Plus, if you spend $40 you will receive 40% off one single bottle of maple syrup with your key chain as part of Sweet Deal Days!
Plus, join in for a Wreath Workshop from 1 - 3 pm!  Workshop cost is $40 .  Register by emailing Jenny at or calling 540-290-1676.
Get your passport stamped here after a tour as part of the Virginia Maple Syrup Trail.

Sugar Tree Country Store
185 Mansion House Road, McDowell
10 am - 5 pm
Check out this unique country store with great selection of gifts for all ages, including new products to offer!
Get your passport stamped here after a tour as part of the Virginia Maple Syrup Trail.

Susanna's Confections
61 Highland Center Drive in the lower level of The Highland Center
10 am - 2 pm
Enjoy delicious baked goods and tasty treats from the following menu, including FREE hot chocolate and a cookie for kids!  
- Assorted chocolate truffles in decorated boxes
- Baklava
- Assorted Christmas cookie trays
- Gingerbread cookies
- Apple strudel
- Pretzels
- Bejgli - walnut & poppyseed roll
- Coffee & Tea

Twice is Nice
168 W. Main Street, Monterey
10 am - 2 pm
Stop by this family clothing thrift store that benefits the Highland Medical Center for a special gift!  Bring in your 2022 Highland County Maple Festival keychain and receive one free item as part of Highland County's Sweet Deal Days!

If you're in Highland County, don't forget to check out our Barn Quilt Trail and the Virginia Maple Syrup Trail.  Check out all our Chamber members and discover other things to do no matter the season!

Learn more about Virginia events at

Highland County

Monterey, VA 24465 United States

Various locations in Highland County

Event Contact
Chris Swecker
Send Email
Saturday, December 3, 2022

Various events all day

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