Shop and savor delicious foods in Winchester’s Old Town easily and effortlessly! Explore titles at the Winchester Book Gallery or equip yourself for outdoor adventures at Mountain Trails.
Children will love exploring the Shenandoah Valley Discovery Museum with its four levels of interactive exhibits and bright box Theater on Pedestrian Mall for shows!
Walk around the Old Town
Old Town Winchester is an essential stop on any trip to Winchester, featuring 250 years of history combined with incredible restaurants and charming shops. Additionally, this walkable downtown district is listed on the National Register Historic District with buildings bearing commemorative plaques.
Loudoun Street Pedestrian Mall is at the core of Old Town and renowned for its restaurants and shops, Civil War museum and historical buildings. Additionally, children can take advantage of summer fun at its south end splash pad while the mall serves as the location of various events throughout the year such as Farmer’s Market or Apple Blossom Festival.
This area of Winchester VA is full of historic sites and one of the top things to do for families with young children. One must-see destination here is Handley Library with its stunning exterior alone worth making the journey; perfect for taking family photos or having lunch in its courtyard! Additionally, music events like Shenandoah University Jazz Band can also be found there on every second Friday each month.
Shenandoah Valley Discovery Museum at 19 West Cork Street is another must-visit. Each floor of this huge museum focuses on different topics; hands-on exhibits for kids provide invaluable educational experiences while being enjoyable; they can pretend to build structures or enter a real beehive!
Shenandoah Valley Discovery Museum boasts not only these interactive displays but also other exhibits which make it one of the best things to do in Winchester VA for kids, such as Water & Play – where children can gain knowledge about water through various interactive demonstrations – but even get to experience life as a paleontologist or doctor through its emergency room simulations!
Old Town offers adults plenty of entertainment. Art lovers will appreciate the monthly First Friday Celebration of the Arts which features gallery events and musicians in cafes and restaurants; you’ll also find a farmers market at Taylor Pavilion every Saturday May-September.
Visit a Museum
Since Winchester takes its history seriously, a visit would not be complete without visiting one of its museums. The Shenandoah Valley Discovery Museum offers interactive exhibits spread out over four floors – perfect for kids! – including stepping inside a giant beehive to learn about honey production or exploring its garden exhibit dedicated to Shenandoah Valley history and art.
Museum of Shenandoah Valley offers another must-visit experience. This expansive space houses Glen-Burnie House and Gardens, a historic home dating back to 1770. Furthermore, miles of trails feature art installations. These special exhibits are open from April until December while all other parts of the museum can be reached year-round.
Vibrissa Brewery at 10 North Kent Street offers indoor and outdoor seating, plus an in-house kitchen staffed by local chefs who serve food prepared by them. Bring in your own dinner to be eaten there at what used to be a newspaper office.
One must-see stop is the historic Hudson River Gothic Revival-style house on Braddock Street where General “Stonewall” Jackson used as his headquarters during part of the Civil War. Today it remains one of the top attractions and still retains much of its original beauty from when Jackson lived there – you’ll even get to see his prayer table, prayer book and family artifacts when touring it!
Half a mile away is Patsy Cline Historic House where she resided from age 16-21. On your tour, you will explore her modest home while learning of her rise to stardom as well as tragic demise; after visiting, pay your respects at her gravesite on Shenandoah Memorial Park Road.
Abrams Creek Wetlands Preserve offers visitors a chance to get outside into nature during their travels, offering visitors a 25-acre calcareous muck fen with rare plants and an excellent example of what these types of wetlands can do for the environment. It’s a wonderful location for hiking or biking adventures alike!
Go Shopping
Winchester shopping center boasts an assortment of boutiques, artisan craft shops, bookstores, and classes such as glass-blowing or pottery making to help visitors develop new skills while vacationing.
Do a walking tour through Old Town shops or take a seat at one of Winchester’s many restaurants for some delicious local cuisine and beverages. Popular choices in Winchester include Red Fox Creamery (146 N Loudoun Street in Winchester) a family-owned business offering homemade ice cream inspired by George Washington; Frenchies Frozen Yogurt Lounge (2214 Papermill Road, Winchester); or the Red Lion Pub and Eatery (236 Main Street in Winchester).
Other popular shops include Battlefield Boots, which specializes in genuine Western boots and accessories; Talbots in Creekside Town Center is well known as an apparel shop for women; Bell’s Men’s & Ladies’ Fine Clothing has earned its name through high quality apparel and accessories for both genders;
Attend the Apple Blossom Festival, held each late spring. This festival lasts six days and provides a great opportunity to explore local crafters and artisans while enjoying live entertainment and delicious concession food!
Wine lovers will have their pick of some of the region’s finest vintages at various wineries and tasting rooms throughout the region, such as The Oak Barrel, Blue Ridge Vineyards and Stone Mountain Winery.
Shenandoah National Park is another natural attraction to consider visiting. Boasting cascading waterfalls, stunning vistas and wooded hollows – making this park popular among hikers and nature enthusiasts. You may also explore some historic sites located nearby.
Go Outdoors
Winchester offers plenty of great outdoor activities for nature enthusiasts. Abrams Creek Wetlands Preserve, the closest larger park to downtown, features a scenic trail through calcareous muck fen that is stroller-friendly; in this preserve are 300 plant species and 180 different birds!
Spend your day hiking at Shenandoah National Park, just a 30-minute drive from Winchester. It offers trails suitable for hiking, mountain biking, horseback riding and fishing; camping facilities are also nearby. There are several museums and historic sites in the area as well; you can explore Native American culture and palaeontology at the Shenandoah Valley Discovery Museum while the Museum of the Shenandoah Valley provides art history exhibits.
Other fun things to do in Winchester include visiting breweries and farms. With its rich apple production history, Shenandoah Valley farms make for the perfect stopover and offer up some fresh apples! While you’re there you can also shop local brands of beef jerky, homemade pies, classic sodas, or old-timey sodas!
Winchester residents looking to do something fun can attend the Apple Blossom Festival every spring. Lasting for one week and drawing over 250,000 attendees each year, this festival provides visitors with an ideal way to sample some of the region’s best wines while taking in beautiful spring weather – it also boasts numerous artisan and crafter booths!
Handley Library may not be your typical library, but it is still worth visiting. Constructed in 1913 and carefully preserved ever since, its historic building offers visitors ample indoor and outdoor space and boasts fascinating artifacts – you could even sign up for a chess match if the mood strikes!
Visit Shenandoah Valley Battlefields National Historic District for another engaging outdoor activity! Take a self-guided tour and learn about key Civil War battles fought here; picnicking or hiking through its scenic trails may also prove rewarding experiences.
