Event Schedule 2021

Kids ROC the Market

Bring your kiddos out the Saturday of Memorial Day weekend for some unique artistic fun and your chance to purchase some local produce and goods from area farmers and artisans.

Hydro dip a wooden plank (supplied) or an item you bring from home with volunteers from Arte Libre VA. How it works

  • Saturday, May 29, 2021
  • 9 am - 12 noon
  • South Street Barn Market @ Woodstock American Legion Parking Lot
  • FREE! Snacks and drinks provided for kids.

Woodstock ROCS (Riley Outdoor Concert Series)

Bring your lawn chair and blanket and enjoy dinner from local food vendors along with live entertainment from regional bands.

W.O. Riley Park Event Lawn and Stage area
Food for purchase beginning at 6:00 pm
Music from 7:00 pm- 9:00 pm.

Free Admission! Entertainment coming soon!

Shenandoah Valley ArtFest

Celebrate and support fine art from The Valley at the second annual Shenandoah Valley ArtFest. Valley artists will fill Court Square with their pieces for sale. Whether you want to exhibit as an artist or want to attend, see more information here!

  • Saturday, June 19, 2021 2:00 - 8:00 pm
  • Musical entertainment - Bill Vaughan and Friends

Vintage Woodstock Festival

Vintage Woodstock Festival is held in annually with dancing in the streets, food, wine & beer, and fun for the entire family! Free Admission!

  • Saturday, June 19, 2021 6:00 - 10:00 pm
  • Music entertainment - E3 with "3 part harmonies, unstoppable grooves, and funky riffs. Their extensive song catalog covers it all; classic R&B, rock, reggae, funk, 80s, 90s, and even today's chart toppers - from Louis Armstrong to Led Zeppelin, from Johnny Cash to The Cure to Coolio."

Independence Day Fireworks 

Free Admission!

  • Sunday, July 4, 2021
  • 9:30 pm - More information
  • Shenandoah County Fair Grounds
  • Rain date Monday , July 5

Kids ROC featuring Marsha from Marsha and the Positrons

Bring the kids out to W.O. Riley Park for 45 minutes of fun songs about science and how the world works with positive social messages. 

  • Saturday, August 7, 2021
  • 9:30 - 10:15 am
  • W.O. Riley Park Rotary Shelter
  • FREE! Snacks and drinks for kids provided.

Luau Pool Party

Join the W.O. Riley Park Pool staff for the first luau pool party with special food, drinks, games, and more!

  • Saturday, August 7, 2021
  • 7 - 9 pm
  • W.O. Riley Park Pool
  • Adults: $5, Ages 6-18: $3, Under 5: Free

Route 11 Yard Crawl

Route 11 Yard Crawl is an annual event held on the second Saturday in August featuring 43 miles of yard and antique sales.

  • Saturday, August 14, 2021
  • 7:00 am - 7:00 pm


If you love tacos, this is your event! WoodsTACO is our annual street taco competition that is unique to the Shenandoah Valley. Purchase your ticket to taste and cast your vote for your favorite taco teams and enjoy music and folklore dancers as well as adult beverages in historic downtown Woodstock. Only 200 tasting tickets sold so purchase yours in advance today! General admission is free and tacos will be available for purchase.

  • Saturday, September 11, 2021
  • 12 noon - 4 pm
  • Downtown/Court Square
  • Rules and team application here

Halloween on Court Square

Halloween on Court Square is our annual tradition involving trick or treating outside of businesses, mask making, pumpkin painting, magic shows and several other children’s activities. This year we will be making some necessary social distancing changes in order to limit the spread of COVID-19. 

  • Saturday, October 30, 2021
  • 11:00 am - 2:00 pm

Small Business Saturday

Shopping local makes a positive impact on our town. Support local businesses this holiday season and shop Woodstock on Small Business Saturday, November 27, 2021.

Shop Small Sweepstakes

If you shop local this holiday season you could win big! Spend some time and money in our participating Woodstock businesses and you are eligible to enter to win a prize basket with items from these businesses. More information.

Light up Woodstock 

Light up Woodstock is held on the Friday evening a week after Thanksgiving featuring a music, parade, wagon rides, visits with Santa on Court Square.

  • Friday, December 3, 2021
  • 5:30 pm - Children’s choirs and tractor pulled wagon rides
  • 6:00 pm - Cookies and hot cocoa in front of historic court house sponsored by Emmanuel Episcopal Church
  • 6:30 pm - Holiday parade begins
  • 6:45 pm - Lighting of the Tree with Mayor McCleary and special guest, Max, on Court Square

Woodstock's Deck the Halls Holiday Display Contest

Instead of COVID-19, let's spread holiday cheer all over Town! Business and home owners within the Woodstock town limits can decorate their property and enter to win in one of the six categories. More information about entering and voting for your favorite displays can be found here.

Holiday Scavenger Hunt

Load your family/friends in the car and find Santa's Woody Woodstock characters all around Town! List of locations TBD.

For more information, contact the Director of Marketing and Events or (540) 459-3621