Local Events

2016 Local Events

58th Annual Highland County Maple Festival

March 11th and 12th, 2016 (First Weekend)
March 18th and 19th, 2016 (Second Weekend)

We are booked up during this event and also for 2017. Contact us to be placed on the waiting list. We note that we require a two night stay during festival weekends.

Take a step back in time to Highland County, “Virginia’s Switzerland.” Travel back roads and mountain byways to the annual Highland Maple Festival event. Held on the 2nd and 3rd weekends of March, the Maple Festival has been an annual event in Highland County, Virginia, since 1958.

Website: http://www.highlandcounty.org/events/maple-festival/

Lions Club Street Dance

Date: Saturday, July 9, 2016
Enjoy country entertainment with bluegrass music, cake walks, square dancing, food and clogging at the annual Lions Club Street Dance. Fun for the entire family. This event is located on Spruce Street and routinely goes 5 P.M. until dark.

Old Time Fiddler’s Convention

Date: Thursday – Sunday, July 14 – 17 , 2016
The Highland Old Time Fiddlers Convention will hold its third annual competition at the Highland County Fairgrounds. A contra dance will be held Thursday night at 7 PM and is free to the public. Competition will start Friday at 4 PM and will continue at 11 AM on Saturday. Food will be available on the grounds. Prizes will be awarded in all old time categories and will be announced by 7 PM Saturday at which time there will be a top 5 play off. Sunday at 10 AM, there will be a hymn-sing that is free to the public. Admission to the competition is $5 on Friday and $10 on Saturday with children under 12 free.

Website: www.highfiddle.com

Mountain Mama Road Bike Challenge

Date: Saturday, August 6th, 2016

We are booked up during this event. Please contact us to be placed on the waiting list.

10,000 Feet of climbing, up to 100 mile routes, 6 mountains, 3 counties, 2 states. A fundraiser to benefit Highland County Recreation Commission sponsored programs and facilities. Challenging ascents, thrilling descents, rolling valley roads and breathtaking views from high atop the mountains of the Allegheny Highlands guarantee a challenge for all cycling skill levels.

Website: www.highlandcountyrecreation.org
Buy prints & digital downloads from the event: Mirrorslap Photography

4th Annual Bluegrass Valley Music Festival in Blue Grass, VA

Date: Friday – Sunday, August 12- 14, 2016
A weekend of camping and fun for all ages with great bands, good food, craft beer, and local vendors such as Mirrorslap Photography and Sarahcycled!

Website: www.bgvmusicfestival.com
Facebook: https://www.facebook.com/bluegrassvalleymusicfest

Highland County Fair

Date: Wednesday – Saturday, August 31 – September 3, 2016
An old-time country fair steeped in tradition! Celebrating 62 years, the Highland County Fair opens with a hometown parade that winds its way through the streets of historic Monterey on the Wednesday preceding Labor Day.

Website: www.highlandcountyfairva.com

Highland County Farmers Market

June – September, every Friday afternoon from 3:30 p.m. – 6:00 p.m.
The market is located in Monterey, Virginia at 61 Highland Center Drive Monterey, VA 24465. It features a selection of organic food, local specialties, vegetables, fruits, and local arts + crafts.

Website: http://www.highlandcounty.org/events/farmers-market/

Fall Foliage of 2016

September 25th – October 25th, 2016
So, you’re interested in seeing some of the beauty that is Virginia during Fall Foliage season? But you don’t want to fight the traffic that clogs some of the best-known places, such as Skyline Drive or the Blue Ridge Parkway? Come visit the breathtaking mountain views of Highland County, VA and fill your eyes with wide swatches of vibrant yellows, reds and oranges.

Our guest rooms quickly fill up during the Fall Foliage season so call or email to make a reservation today. A two night minimum is required for all weekends in October.

Hands & Harvest Festival

Date: October, Friday & Saturday, October 7 – 8, 2016
Celebrate the beauty of Autumn at Highland County’s annual Hands & Harvest Fall Foliage Festival. Held on the second weekend in October on Columbus Day weekend, this event offers two full days of activity and entertainment. Come and observe the mountain forests of Virginia’s Western Highlands transformed into a rich palette of russet, gold, and scarlet. Used Book Sale at the Highland County Public Library, SPCA Annual Sweater Sale, Arts & Crafts Show with vendors on the Courthouse lawn, Farmers’ Market with freshly baked goodies at the Highland Center, Antique Appraisal Fair, and more!

Take time to explore the back roads by enjoying one of Highland County’s Scenic Driving Tours or Barn Quilt Trails.


December, Friday & Saturday, 2 – 3, 2016
Join us this holiday season and celebrate an old fashioned Christmas complete with carolers, hot apple cider, maple pecan pie, the annual tree lighting ceremony, holiday craft show at the Highland Center, and more.

Website: http://www.highlandcounty.org/events/wintertide/