First Night Winchester:  Each and every year you can ring in the New Year with family and friends at this annual festival of the arts! Festivities include a wide variety of live performances, lots of surprises, and the famous “Apple Drop” culminating in an amazing fireworks display at midnight… annually on December 31st, in and around Old Town Winchester.

In and around Old Town Winchester
(540) 533-5561

Shenandoah Apple Blossom Festival:  A family-friendly festival that includes more than 30 events: band competitions, dances, the world’s largest firefighter’s parade, a Grand Feature Parade, a circus, a 10K race, carnival, celebrities guests and appearance, a Weekend in the Park featuring hundreds of crafters, food, fun, fireworks, and much more… annually in late April and early May.  All over and around Winchester, VA!

“Of Ale and History” Beer Festival at the Belle Grove Plantation:  Virginia’s longest running beer festival never fails to disappoint the throngs of attendees.  Sample an array of beers from the New and Old World. Music provided by live bands, food, and tours of the historic home, all in a scenic outdoor setting… annually in May.

336 Belle Grove Rd.
Middletown, VA 22645
(540) 869-2028

Newtown Heritage Festival:  A free family festival that celebrates the town of Stephens City’s heritage and includes wagon rides, a parade, a car show, a craft show, and an incredible fireworks show, The Newtown Heritage Festival promotes the Historical Significance of Stephens City and its environs and fosters a sense of community pride. This is accomplished through a family-oriented weekend of events that showcases the past and present of the area… annually in May, Memorial Day Weekend.

5165 Main Street
Stephens City, VA 22655
(540) 869-3087

Virginia Herb Festival:  Live music, unique vendors and educational workshops on the use of herbs, and wine and beer tastings. The Virginia Herb Festival was founded in 2009 by Sunflower Cottage in Middletown, VA. Sunflower Cottage is a herb farm and garden center that sits on 40 acres of farm land in the Shenandoah River Valley. We provide fun and entertainment centered around the delight in herbs and the agrarian lifestyle. With the expansion of our business including an awesome farm brewery, this festival is great fun for everyone in the family… annually, the second week of June.

150 Ridgemont Rd.
Middletown, VA 22645
(540) 869-8482

Frederick County Fair:  Livestock, petting zoo, pageants, demolition derby, tractor pulls, monster trucks, educational exhibits, a carnival, live music, and traditional fair food are just some of the reasons to come to the fair… annually, the last week in July.

167 Fairground Road
Clear Brook, VA 22624
(540) 667-8739

Fourth of July Fireworks and Independence Day Celebrations: Winchester, Stephens City, and Middletown host Independence Day events with family activities and spectacular fireworks displays… Winchester’s event is held on July 3.

Old Town Winchester
33 E. Boscawen Street
Winchester, VA 22601
(540) 535-3661
Sherando Park
200 Lakeview Circle
Stephens City, VA 22655
(540) 665-5678
Middletown Community Park
Senseney Avenue
Middletown, VA 22645
(540) 869-2226

Peach, Apple, and Pumpkin Harvest Festivals: Marker Miller Orchards and Richard’s Fruit Market host harvest festivals on their scenic farms. Featuring live music, pick-your-own, children’s activities, wagon rides, and delicious foods… annually Peaches in August, Apples and Pumpkins in October.

Richard’s Fruit Market, (540) 869-1455
Marker Miller Orchards (540) 662-1980

Route 11 Yard Crawl:
Prepare yourself for a treasure hunter’s dream. 43 miles of yard sales stretch from Stephens City to New Market, Virginia.  The Route 11 Yard Crawl is over 40 miles of yard sales and business sales along the Old Valley Pike, U.S. Route 11. There is no official starting point for the crawl, however the official crawl is from New Market to Stephens City. You may start at any point…. second Saturday in August.

Stephens City and South to Middletown along Route 11
(877) 871-1326

Walking in a Winter Wonderland:  Stroll through a winter wonderland and enjoy holiday music, cookies, and hot chocolate as thousands of lights reflect off the lake at Clearbrook Park. Warm up in the log cabin where you might be lucky enough to see Santa and Mrs. Claus… Thanksgiving Friday – First week of January.

Clearbrook Park
112 Clearbrook Dr.
Clear Brook, VA 22624
(540) 665-5678

Christmas Candlelight and Daytime Tours of Belle Grove Plantation:  Enjoy the magic of an old-time Shenandoah Valley Christmas. The plantation house is beautifully decorated for the holidays by area garden clubs, much as it would have been when its original residents occupied it… annually throughout December.

Belle Grove Plantation
336 Belle Grove Rd.
Middletown, VA 22645
(540) 869-2028

Candlelight Tours of Historical Society Museums:  Delightful, free holiday tours of Abram’s Delight, Stonewall Jackson’s Headquarters, and George Washington’s Office by candlelight. Local garden clubs decorate the museums in seasonal greenery… annually late November through early December.

1340 S. Pleasant Valley Rd.
Winchester, VA 22601
(540) 662-6550

Anniversary Reenactment of the Battle of Cedar Creek:  Civil War reenactment on the original grounds. Cavalry, artillery, infantry and civilian demonstrations, and battles daily. Sutlers, food, symposia, music, and candlelight tours of camps… annually during the third weekend in October.

8437 Valley Pike
Middletown, VA 22645
(540) 869-2064

Shenandoah Valley Apple Harvest Festival:  Held annually for over 40 years, this festival celebrates everything apples! It includes an arts and crafts show, live music, food vendors, apple pie eating contest, apple butter making, antique car show, bingo, inflatables and facepainting for children, craft beer and hard cider tastings, and more… annually during the third weekend in September.

155 Fairground Rd.
Winchester, VA 22624
(540) 336-9114

Winchester Greek Festival:  Sample delicious culinary fare and experience Greek music and dance…fun for the whole family!  For over 50 years, the Dormition of the Virgin Mary Greek Orthodox Church has provided the spiritual needs of Eastern Orthodox Christians in the beautiful Northern Shenandoah Valley. Located in the historic City of Winchester, our congregation aptly reflects the American experience and is comprised of approximately 100 families representing several different Ethnic and Cultural groups… annually during the third Weekend in August.

1700 Amherst St.
Winchester, VA 22601
(540) 667-1416

Civil War Weekend:  Civil War sites throughout Winchester and Frederick County offer unique opportunities to experience life during the war. Tours, living history demonstrations, children’s activities, and more create an unforgettable experience. For more information, contact the Visitors Center… annually in August.

1400 S. Pleasant Valley Rd.
Winchester, VA 22601
(877) 871-1326

Shenandoah Valley Tastefest:  See cooking demonstrations and taste dozens of varieties of tomatoes and garlic. Meet vendors selling garden products and garlic and tomato-related foods, gifts, and kitchen gadgets… annually the last Saturday in August.

901 Amherst St.
Winchester, VA 22601
(888) 556-5799