Sports Enthusiasts – Let's Get Active!
Thursday, April 25
MID-DAY
Arrive in beautiful Old Town Winchester to your reservation at the George Washington Hotel, or if you prefer to be away from the crowds, just a few miles away at the Microtel Inn & Suites, Spark by Hilton, Tru by Hilton or Hilton Garden Inn.Winchester has a lot of historic AirBnB options as well. Prepare for a great night’s rest in anticipation of a weekend full of activity.
Friday, April 26
MID-DAY
Choose from one of our many athletic events we have to offer over the weekend. Pickleball is the fastest growing sport in America and the Shenandoah Apple Blossom Festival will feature a clinic, exhibition, and reception on Friday evening as well. Golf fanatics are sure to love our Golf Classic that begins at noon at Rock Harbor Golf Course. If tennis is more your speed, participate in the 3-day Stonebrook Club Tennis Tournament.
EVENING
Take a walk on the Old Town Winchester walking mall and check out the 30+ restaurant options for dinner. With options like Union Jack Pub & Restaurant, Roma Old Town Wood Fired Pizzeria and Alesatian Brewing Company, and El Centro, there are options for everyone in the family.
Saturday, April 27
MORNING
Join us to play everyone’s new favorite sport and be a part of our second annual Pickleball Tournament for men’s and women’s doubles.
MID-DAY
If Esports is more your thing, you can join the Esports Free Play event at Bright Box Theater in Old Town Winchester.
MID-DAY
Arrive in beautiful Old Town Winchester to your reservation at the George Washington Hotel, or if you prefer to be away from the crowds, just a few miles away at the Microtel Inn & Suites, Spark by Hilton, Tru by Hilton or Hilton Garden Inn.Winchester has a lot of historic AirBnB options as well. Prepare for a great night’s rest in anticipation of a weekend full of activity.
Friday, April 26
MID-DAY
Choose from one of our many athletic events we have to offer over the weekend. Pickleball is the fastest growing sport in America and the Shenandoah Apple Blossom Festival will feature a clinic, exhibition, and reception on Friday evening as well. Golf fanatics are sure to love our Golf Classic that begins at noon at Rock Harbor Golf Course. If tennis is more your speed, participate in the 3-day Stonebrook Club Tennis Tournament.
EVENING
Take a walk on the Old Town Winchester walking mall and check out the 30+ restaurant options for dinner. With options like Union Jack Pub & Restaurant, Roma Old Town Wood Fired Pizzeria and Alesatian Brewing Company, and El Centro, there are options for everyone in the family.
Saturday, April 27
MORNING
Join us to play everyone’s new favorite sport and be a part of our second annual Pickleball Tournament for men’s and women’s doubles.
MID-DAY
If Esports is more your thing, you can join the Esports Free Play event at Bright Box Theater in Old Town Winchester.
Thursday, May 2
MORNING
Start the day off at our Breakfast Walk. Enjoy a beautiful walk around the Museum of the Shenandoah Valley followed by a light, refreshing breakfast. You can choose to stay and enjoy the rest of the museum and gardens or attend one of the many events that follow the breakfast walk like the prestigious Queen’s Dinner or enjoy dueling DJs at the Ultimate Dance Party.
Friday, May 3
MORNING
Soak up some sun while you hike the Museum of the Shenandoah Valley North Loop or the Third Winchester Battlefield Park: Red Bud Run Trail. Both trails loop back to the start, and the hike will be a great way to explore the beautiful scenery of the Shenandoah Valley.
AFTERNOON
Afterwards, let your kids shine and make new friends at the Kids’ Bloomin’ Mile Race on the John Handley High School campus. After they’re done racing their hearts out, your family can stay and enjoy the Firefighters’ Parade featuring engines they saw at the rodeo followed by the well-loved Music Fest & Fireworks Show.
Saturday, May 4
MORNING
Start off the morning by choosing to participate in the 10K Race or attending our Sports Breakfast. The Sports Breakfast begins at 8 a.m. at the Tolley Dental Zone. Have the chance to meet and listen to your sports heroes in a more personal setting. Our 10K Race starts bright and early at 8:30 a.m. at the John Handley High School campus. Break your personal record while running the beautiful, historic streets of Winchester. When you’re done, head down to Old Town for the second day of Midway or stick around for our Grand Feature Parade.
EVENING
End the night by sending your teens to the Boom Bloom. They are sure to dance the night away and make Instagram worthy memories. You may also decide to dust off your cowboy boots and take the family to the Country Music Party to listen to 2021 American Idol winner Chayce Beckham and special guest Davisson Brothers Band. These are a guaranteed way to end your weekend on a fun note.
MORNING
Start the day off at our Breakfast Walk. Enjoy a beautiful walk around the Museum of the Shenandoah Valley followed by a light, refreshing breakfast. You can choose to stay and enjoy the rest of the museum and gardens or attend one of the many events that follow the breakfast walk like the prestigious Queen’s Dinner or enjoy dueling DJs at the Ultimate Dance Party.
Friday, May 3
MORNING
Soak up some sun while you hike the Museum of the Shenandoah Valley North Loop or the Third Winchester Battlefield Park: Red Bud Run Trail. Both trails loop back to the start, and the hike will be a great way to explore the beautiful scenery of the Shenandoah Valley.
AFTERNOON
Afterwards, let your kids shine and make new friends at the Kids’ Bloomin’ Mile Race on the John Handley High School campus. After they’re done racing their hearts out, your family can stay and enjoy the Firefighters’ Parade featuring engines they saw at the rodeo followed by the well-loved Music Fest & Fireworks Show.
Saturday, May 4
MORNING
Start off the morning by choosing to participate in the 10K Race or attending our Sports Breakfast. The Sports Breakfast begins at 8 a.m. at the Tolley Dental Zone. Have the chance to meet and listen to your sports heroes in a more personal setting. Our 10K Race starts bright and early at 8:30 a.m. at the John Handley High School campus. Break your personal record while running the beautiful, historic streets of Winchester. When you’re done, head down to Old Town for the second day of Midway or stick around for our Grand Feature Parade.
EVENING
End the night by sending your teens to the Boom Bloom. They are sure to dance the night away and make Instagram worthy memories. You may also decide to dust off your cowboy boots and take the family to the Country Music Party to listen to 2021 American Idol winner Chayce Beckham and special guest Davisson Brothers Band. These are a guaranteed way to end your weekend on a fun note.