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Saturday, December 2, 2023


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!

*** Below, you'll find information about the 2023 Wintertide that was held on Saturday, December 2nd ***

*** Please check closer to the 2024 event for updates, scheduled for Saturday, December 7th ***

December 2, 2023

The Highland Center
61 Highland Center Drive, Monterey
10 am - 5 pm Wintertide Market with Local Vendors and Kids' Activities
Interested in being a vendor at the Wintertide Market at The Highland Center in Monterey from 10 am - 5 pm on December 2, 2023?  Click here for the application and full details!
11 am - 3 pm Susanna's Confections is open for tasty treats! Plus, children get a free hot chocolate and cookie!
11 am - 1 pm Visit with Santa

Special thanks to Blue Grass Valley Bank for sponsoring the Christmas tree!
Special thanks to Highland Children's House for decorations for the tree!

Highland County Christmas Parade
Begins at the Highland County Public School Parking lot at 240 Myers Moon Road in Monterey through downtown Main Street and Spruce Street to completion at The Highland Center
5:30 pm The Highland County Recreation Commission is bringing the festive event back! Email to participate with a float!

Big Fish Cider, Co.
59 Spruce Street, Monterey
2 - 7 pm
Drop by Saturday afternoon for a free cup of hot mulled cider (nonalcoholic) and pick up unique Highland County gifts like local maple syrup, honey, and, of course, cider!

Blue Grass Mercantile
2558 Blue Grass Valley Road, Blue Grass
9 am - 7 pm
It's "Wintertide Shrimp Fest"!  Enjoy this special of delicious steamed shrimp (available all weekend)!  Plus, get 1/2 off this special (1 per customer) and other daily specials with your 2023 Maple Festival Keychain as part of Sweet Deal Days

Charles Pinckney Jones House Museum
144 West Main Street, Monterey
10 am - 7 pm
Enjoy Highland County's newest museum with the downstairs decorated for Christmas!

Claire's Cakes & Cafe
107 West Main Street, Monterey
9 am - 2 pm, with drop-in cookie decorating from 2:30 - 5:30 pm
Breakfast, lunch, baked goods, cakes, coffee & catering! Stop in for yummy seasonal items.  Bring the kids for a fun drop-in cookie decorating class from 2:30 - 5:30 pm!

Ginseng Mountain Farm & Store
6359 Potomac River Road, Blue Grass
12 - 5 pm
30th Anniversary Celebration!  Stop by this "new time" country store north of Monterey to enjoy goodies while you shop and draw for a 5 - 30% discount on your purchase!

Heart and Soul Massage School
125 West Mill Alley, Monterey
4 - 7 pm
Annual Holiday Open House!  Heart and Soul Massage School & Spa, and The Rock Shop will be open Saturday, December 2nd from 4 - 7 pm!  They will have specials on massage gift certificates and specials on rock shop items!

Highland Roots Market
11 E. Main Street, Monterey
10 am - 6 pm
Stock up on gifts, produce, and groceries at this back-to-basics food mart!  Bring in your 2023 Highland County Maple Festival keychain and receive 10% off as part of Sweet Deal Days!

High's Restaurant
73 W. Main Street, Monterey
11 am - 8 pm
Surf and Turf Special!  High’s Restaurant will be offering its Surf and Turf Special this Wintertide Weekend:16 oz., Inch Thick, Ribeye Steak with Our famous Hand Breaded Shrimp, Two Sides and a Scoop of your choice of 8 flavors of ice cream!  On Sale for $29.95.  No limit per customer!

Jenny Wren Gatherings
81 W. Main Street, Monterey
11 am - 7 pm
Check off your holiday shopping list with eclectic treasures and local arts & crafts with so much to choose from!  Need lodging for Wintertide?  Two-night weekend lodging is available in the cozy Nest Rental cabins in the heart of Monterey at the Robin's Nest and Chickadee Cottage!  

Monterey Inn Lodging and Restaurant
32 West Main Street, Monterey
Breakfast from 8 am - 11 am; Lunch from 11 am - 3 pm; Front desk from 8 am - 8 pm
New! The Monterey Inn will be adding dinners every Saturday from 5 - 9 pm by reservation only starting on December 2 - contact the Monterey Inn at or 540-495-0070 to reserve your space!
Plus, they’ll be offering restaurant gift cards for sale: buy a $50 gift card and get a $10 bonus gift card for the Monterey Inn Restaurant!

Sugar Tree Country Store
185 Mansion House Road, McDowell
10 am - 5 pm
Check out this unique country store with a 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
11 am - 3 pm
Stop on in for tasty treats.  Plus, children get a free hot chocolate and cookie!

Twice is Nice
168 W. Main Street, Monterey
10 am - 7 pm
Stop by this family clothing thrift store that benefits the Highland Medical Center for a special gift!  Bring in your 2023 Highland County Maple Festival keychain and receive one free item as part of Sweet Deal Days!

Spread holiday cheer with the entire family throughout December by entering the following!
Highland County Recreation Commission's Holiday Lights Contest - Click here for full details!
Blue Grass Valley Bank's Holiday Color Contest - Click here for full details!


Want deals during Wintertide?  Check out our Sweet Deal Days promotion!

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 2, 2023

Various events all day

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