Free things to do in Winchester: the Trails at the MSV, Kernstown Battlefield, the Green Circle, the mural trail and free festivals through the year.

Last checked Oct. 19, 2026. “Free” means the organizer or site says there is no admission charge, on the pages linked below. Parking, food and extras may cost money.

A lot of what Winchester does best costs nothing: walking the Loudoun Street Mall and the Green Circle Trail, the art park at the Museum of the Shenandoah Valley, a Civil War battlefield on the edge of town and a run of free festivals through the year.

Plan ahead

Outdoors

  • The Trails at the MSV, 901 Amherst St. A free 90-acre art park with about 3 miles of trails, outdoor art, a stone circle, a treehouse and grassy picnic mounds, open daily from 7 a.m. to dusk (MSV trails page).
  • Green Circle Trail. The city’s 6.06-mile walking and biking loop through Jim Barnett Park, Old Town and the Abrams Creek Wetlands Preserve; see our trails guide.
  • Abrams Creek Wetlands Preserve, off West Jubal Early Drive: a 25-acre fen with a boardwalk, more than 300 plant species and 180 kinds of birds, and a free self-guided audio tour. The city runs guided nature walks in spring and fall (preserve page).
  • Jim Barnett Park, 1001 E. Cork St.: playgrounds, a fishing lake, disc golf, the par course, an arboretum of about 100 trees and the free Winchester Dog Park (Jim Barnett Park; dog park). Parks are open dawn to dusk.

History

  • Kernstown Battlefield, 610 Battle Park Drive. Site of the First and Second Battles of Kernstown; open seven days a week, 10 a.m. to 4 p.m., with free admission (donations welcome). Guided tours of the battlefield and the Pritchard House run Friday to Sunday through Nov. 1, 2026, and by appointment (Kernstown Battlefield).
  • Hollingsworth Mill exhibit, next to Abram’s Delight, 1340 S. Pleasant Valley Road: a free exhibit for America’s 250th birthday about Daniel Morgan, with artifacts from the 1876 Centennial and the 1976 Bicentennial (Winchester-Frederick County Historical Society).
  • Cedar Creek and Belle Grove National Historical Park, Middletown: no entrance fee (NPS fees page). The NPS visitor center, 7712 Main St., Middletown, is open Wednesday to Sunday, 9 a.m. to 4:30 p.m., May through October, and Friday to Sunday, 10 a.m. to 4 p.m., November through April (NPS hours). Partner sites set their own admission.
  • Winchester National Cemetery, 401 National Ave.: open daily from dawn to dusk (VA cemetery page).

Old Town on foot

  • The Loudoun Street Mall, the car-free heart of a 45-block historic district. Meters are free on weekends and after 6 p.m. (Old Town guide).
  • Old Town Mural Trail, more than a dozen murals in alleys and on buildings, including two of Patsy Cline (mural trail map).
  • History of Us, Friends of Old Town’s self-guided walking tours of the downtown buildings and the people behind them (Friends of Old Town).
  • First Fridays, Friends of Old Town’s monthly evening on the mall (events).

Free festivals (2026 dates)

  • Apple Blossom Antique Car Show, Jim Barnett Park, May 9, 2026: free, family-oriented (2026 listing).
  • Juneteenth Celebration, Loudoun Street Mall, June 19, 2026: Hood-Love’s free evening of speakers, vendors, music and kids’ activities (2026 listing).
  • Patsy Cline Block Party, Patsy Cline Historic House, 608 S. Kent St., Sept. 5, 2026: free, held every year on the Saturday of Labor Day weekend (Labor Day guide).
  • Colonial Costume and Dance, Winchester-Frederick County Visitors Center, Sept. 6, 2026: free presentations (2026 listing).

Seasonal free events, from parades to tree lightings, are on our Christmas parade and tree lighting and Fourth of July fireworks pages.

What this means for you

  • Kernstown and the MSV trails are free every day; pair them for a history-and-outdoors day.
  • Save Old Town for a weekend, when parking at meters is free too.
  • Check the visitors bureau and Friends of Old Town calendars for this year’s free festival dates.

Related: parks and trails, dog-friendly Winchester, kids’ activities and things to do this month.

Frequently asked questions

Is the Kernstown Battlefield free?

Yes. The Kernstown Battlefield, 610 Battle Park Drive, is open seven days a week from 10 a.m. to 4 p.m. with free admission; donations are welcome, according to the Kernstown Battlefield Association.

Are the Trails at the Museum of the Shenandoah Valley free?

Yes. The Trails at the MSV, a 90-acre art park at 901 Amherst St., are free and open daily from 7 a.m. to dusk. The museum galleries and gardens charge admission.

What free events are there in Winchester?

In 2026 the Patsy Cline Block Party on Labor Day weekend, Hood-Love’s Juneteenth celebration on the Loudoun Street Mall and the Apple Blossom Antique Car Show at Jim Barnett Park were all free, according to their organizers.

Is Cedar Creek and Belle Grove National Historical Park free?

The National Park Service charges no entrance fee for Cedar Creek and Belle Grove National Historical Park. Partner sites in the park set their own admission.