Wintertide

The Highland Center's Annual Wintertide Vendor Market and Activities
61 Highland Center Drive, Monterey
9 am - 3 pm • Wintertide Holiday Vendor Market with Local Artists and Crafts
9 am - Noon • Kids Activities with the 2025 Maple Queen Court
10 am - Noon • Visit from Santa
11 am - 1 pm • Food Available
1 pm • Allegheny Mountain Strings Performance

Interested in being a vendor at the Wintertide Market? Contact The Highland Center at 540-468-1922.

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

*** Bonus Event on Sunday, December 7, 2025 ***
3 pm • Highland Community Orchestra will perform a free concert on Sunday, December 7, 2025 at The Highland Center in Monterey  (Additional concert later that night at 7 pm at Pocahontas County High School in West Virginia)

 

Christmas on Main Street
165 W. Main Street, Monterey at the Highland County Courthouse Lawn
4 pm • Before the parade, grab some Christmas cheer!  Enjoy the following activities and more:

• Highland County Girl Scouts selling hot chocolate and other food - warm up with cookies, maple hot dogs, chili and cornbread!
• Highland County Recreation Commission selling Christmas Trees on a first-come, first-serve basis
• Highland FFA selling wreaths
• Christmas music on The Curly Maple balcony from Scott Smith

 

Highland County Christmas Parade
Begins at the VDOT Parking lot at 1005 Fleisher Avenue in Monterey through downtown Main Street and Spruce Street to completion at The Highland Center
5 pm • The Highland County Recreation Commission is hosting this growing festive event.  Email director@highlandcountyrecreation.org for full details and to participate with a float!

 

Charles Pinckney Jones House Museum
144 West Main Street, Monterey
Noon - 7 pm
Enjoy Highland County's newest museum!

 

Highland County Department of Social Services Angel Tree
158 Courthouse Lane
Monday - Friday between 8:30 and 4:30 pm

The Highland DSS Child & Adult Angel Tree is officially up and ready!

Help spread holiday cheer to Highland County residents in need! This special program supports local adults and children who receive SNAP, Medicaid, Adult Services, or Adult Protective Services by providing them with extra holiday assistance.

Want to make someone’s season brighter? Stop by Highland DSS at 158 Courthouse Lane, Monterey, VA between 8:30 AM – 4:30 PM, Monday through Friday to pick up an angel. Can’t make it in person? No problem — just email hannah.murray@dss.virginia.gov or call 540-468-2199 ext. 307 to request one.

All gifts must be returned to Highland DSS no later than December 8th. Each angel envelope includes important instructions for wrapping, labeling, and gifting — please follow them carefully.

Thank you for helping make the holidays a little brighter for our Highland County neighbors!

 

Highland County Visitor Center
27 West Main Street, Monterey
11 am - 9 pm
Browse Highland County info, and check out our one-of-kind maple syrup themed brochure display, located in the Highlander!

 

Holiday Shoppe at The Barn at Monterey Inn
32 West Main Street, Monterey
1 - 5 pm
FREE EVENT: Step into the magic of the season at our Holiday Shoppe, a joyful community event designed for the whole family!
 Highlights include:
•  Secret Kids’ Shopping Area – Kids can choose special gifts for their family members with the help of a friendly personal shopper! (Gifts are affordably priced and wrapped for that perfect surprise!)
•  Arts & Crafts Corner – Children can get creative making holiday crafts to take home or give as gifts.
•  Holiday Café & Hot Chocolate Bar – Sip a warm cup of cocoa and indulge in delicious Christmas-themed desserts and seasonal treats.
•  Adult Gift Vendors – Find unique, handcrafted, and locally made gifts for everyone on your list.
•  Family Photo Opportunities – Capture the magic of the holidays with festive decorations!
RSVP needed by November 30th by emailing reservations@montereyinnva.com.  Every week, a winner will be drawn for a $20 gift certificate to use in the secret shopping area.

 

Twice is Nice
168 West Main Street, Monterey
10 am - 7 pm
Stop by this family clothing thrift store that benefits the Highland Medical Center for a special gift!

 

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

Learn more about Virginia events at www.virginia.org.