Loudoun Street Mile

Celebrate Memorial Day by running in the Loudoun Street Mile! This event consists of a mile run, a fitness walk, and a tot trot.

This 34th annual edition of the Loudoun Street Mile traverses Loudoun Street in Historic Old Town Winchester, Virginia. This year’s race will again serve as the Collegiate Running Association Championship race. Prize money will be awarded!

COVID-19 UPDATE: Please note that we made many changes to last year’s race in order to comply with COVID regulations. We will do the same this year in an effort to insure another safe event. Please see website for additional information.


Fort Loudoun Day Living History Event

Join us at the French and Indian War site of Fort Loudoun

Bring the family and enjoy a fun day learning about the history of the French & Indian War era at the site of Colonel George Washington’s headquarters for the Virginia Regiment.

Meet living history interpreters including Colonel James Wood, founder of Winchester and mentor to young George Washington, Captain George Mercer and his company of the Virginia Regiment,  and others.

Tours of the Fort site will be offered throughout the day.

The event is put on by The French and Indian War Foundation and is free to the public.

For additional information, visit our website at FIWF.org, or call 419-971-3493.

You can also take an Audio Tour of Fort Loudoun: 703-574-6110.

Mother’s Day Picnic in the Vineyard

Treat your mom to a Mother’s Day picnic at the vineyard! Spend the day with Mom surrounded by the quaint elegance of James Charles Winery.

There are three options for your picnic:
Tarragon Chicken Salad Sandwich with pecans, grapes, celery, and Hellmans with baby greens on croissant.
Ham with Brie cheese, Granny Smith apples, baby lettuce mix and Dijon mustard on hearty grain bread.
Baby spinach with hummus, roasted red peppers, shaved carrots, sliced tomato, feta cheese, balsamic glaze and olive oil

Each wine-country Mother’s Day picnic will include a side salad of baby lettuce topped with tomato, cucumber, Kalamata olives, feta cheese and red-wine
vinaigrette. It even includes a dessert: rockslide brownie bar topped with caramel, toasted pecans, brownie chunks and caramel ganache.

So leave the planning for your Mother’s Day outing to us, and we’ll have your picnic ready for you when you arrive. Due to the popularity of our Mother’s Day events, lawn chairs & blankets are recommended.)

Admission Fee: $25.00

Youth Trout Derby

FREE – Families are encouraged to bring their young anglers (ages 4-14) to catch stocked trout and other fish at Clearbrook Park on Friday evening, May 7th from 5:30-8 pm. This is a rain or shine event with no registration required, but a RSVP is helpful for us to inform you of event updates and future fishing adventures.

Participants must bring their own fishing pole, bait, tackle and gear to reel in that big one. Awards and door prizes are in the works to make for the best fishing experience this year! The Youth Trout Derby will create memories for families that will last forever!

Mojo Mothership at West Oaks Farm Market

Mojo Mothership in concert

Join us for an evening of modern and classic rocking blues in the courtyard at West Oaks Farm Market. Food and beverages will be available from the cafe. Mojo Mothership plays “Funky Southern Fried” Rhythm and Blues.

Apple Blossom Festival Bloomers’ Luncheon

Ladies, “It’s Bloom Time!!” to enjoy the festivities surrounded by your girlfriends with dancing and plenty of fun at the Massage Envy Bloomers’ Luncheon! This ladies-only event will feature the music of Souled Out, a sit-down luncheon from Panera Bread, and an open bar with a variety of draft beers and some selected wines. There will also be a cash bar available with a tantalizing selection of drinks. Enjoy yourselves at the Tolley Dental Zone, Frederick County Fairgrounds, surrounded by your friends. Tickets are $35, which includes your reserved seat, meal, select open bar drinks, and entertainment!

This event is at 11 a.m. on Friday, April 30th. If you plan to enjoy the adult beverages, you must bring a valid ID.
21 and older only.

The Bloomers’ Luncheon is an outdoor open tent event at the Frederick County Fairgrounds. This is a rain or shine event.

COVID-19 Statement: Ticket holders will be required to follow CDC guidelines and mandates in order to participate in events.

Apple Blossom Festival: Tennis Tournament

The Shenandoah Apple Blossom Festival® is excited to announce the return of its annual USTA-sanctioned tennis tournament. Now in its fifth year, the event promises to be competitive and exciting for tennis players of all levels. The success of the tournament grows each year, attracting local and out-of-town tennis players and spectators.

Registered participants receive gift bags filled with tennis-themed items or locally sourced goodies. Trophies are awarded to champions in each division.

The Stonebrook Club of Winchester offers nine courts: four indoor and five outdoor. Two of the outdoor courts are clay-surfaced and lit for evening play. The facility is in a lovely area of rolling hills and blooming orchards in beautiful Winchester.

As the event date approaches, participants and spectators are encouraged to check for updates on this event page, via e-blasts to our fan base, or Social Media. You may also contact the Tennis Tournament Committee at sabftennis@gmail.com

MLB Jr. Home Run Derby


We will be hosting a Major League Baseball® Jr. Home Run Derby on Preston Field in Jim Barnett Park. Pre-registration is required. Boys and girls will be divided into two age divisions (12U and 14U), and will have the chance to advance through three levels of competition. The Local Champions from both age divisions will advance to the Regional Level, and Regional Champions will advance to the Finals, which will take place during the 2021 MLB® All-Star Week™.

All participants should register online. Visit https://www.winchesterva.gov/parks/specialevents for the link.

Battle of First Kernstown Anniversary

The Kernstown Battlefield will be open on this special day to commemorate the 159th Anniversary of the First Battle of Kernstown. Tours of the battlefield will be available, and the battlefield Visitors Center and gift shop will also be open.

Kernstown Battlefield will officially open for the 2021 season on April 10.

Trivia Night at Alamo Drafthouse

Join us for a night of trivia with DJ Skyhigh at the Alamo Drafthouse Cinema in Winchester, VA.

Bring your team and register when you arrive.

Prizes and plenty of fun!