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 Fir Christmas Trees for $45 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 or call 540-468-2978 for full details. (Registration is not needed to participate in the float.  Everyone will need to be at the VDOT parking lot area by 4:50 pm).

 

Art on Main at The 3rd Space
132 West Main Street, Monterey
10 am - 5 pm
Extended hours at this curated gallery featuring local art including pottery, basketry, photography, textile art, stained glass, ornaments, jewelry, woodcrafts, and more!

 

The Barn at Monterey Inn Holiday Shoppe
32 West Main Street, Monterey
Noon - 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.

 

Big Fish Cider, Co.
59 Spruce Street, Monterey
2 - 7 pm, with Wintertide Trivia starting around 7 pm after the Parade
Come on out after the Wintertide Christmas parade for trivia!  Donations will be collected (and matched up to $250) and will go to the Highland County Humane Society.

 

Ginseng Mountain Farm & Store
6359 Potomac River Road, Blue Grass
Noon - 5 pm
Enjoy goodies while you shop and draw a 5% - 15% discount!  Shop for grass fed beef, lamb and sheepskins from our farm, Wolf Creek Calendars, candles, braided rugs, books for country living, local maple syrup, honey, sauces, wool earmuffs, scarves, hats, dusters, baskets, snowflakes, glass sun catchers, wreathes, kissing balls, and Christmas decorations.

 

Highland County Chamber of Commerce Open House and Ribbon Cutting
224 West Main Street, Monterey
3 - 4 pm (3:30 ribbon cutting)
Swing in for a visit to our new office, enjoy light refreshments, and celebrate with a ribbon cutting!

 

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 Fraternal Order of Eagles #4556
43 Potomac River Road, Monterey
9 am - 8 pm
Enjoyed baked items and crafts from 9 am - 3 pm.  The public can enjoy hot chocolate from 4 - 8 pm.  Members and invited guests can enjoy breakfast and dinner of a tenderloin meal.

 

Highland County Public Library
31 North Water Street, Monterey
1 - 3 pm
Christmas Movie Matinee: "The Best Christmas Pageant Ever"

 

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!

 

Southernmost Maple
7738 Big Valley Road, Bolar
9 am - 5 pm
Shop with a multi-generational family of maple syrup producers for your special gifts. Enjoy free coffee while you browse unique items like pure Highland County maple syrup, apple butter, cheese, butter, homemade fruitcakes, Amish rockers, custom wildlife cabinets, and much more!

 

Sugar Tree Country Store
185 Mansion House Road, McDowell
10 am - 5 pm
Come see what this unique old-time general country store offers for your holiday shopping!

 

Townsend Draft Goods
10677 Mill Gap Road, Monterey (14 miles south of Monterey in Mill Gap on Rt. 84)
11 am - 5 pm
Shop unique Christmas gifts at Townsend Draft Goods on Saturday, December 6th from 11 - 5 pm in our warehouse barn in Mill Gap!  Free gift wrapping and 10 percent Wintertide Discount on all orders!  Shop online & get free local delivery at www.TownsendDraftGoods.com.

 

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.