Things to do with kids in Winchester: Jim Barnett Park playgrounds, free library story times, the Discovery Museum, indoor pools and rainy-day picks.

Last checked Oct. 19, 2026. Times and rules come from each place’s own website or the city’s pages, linked below. Library programs change month to month; check the calendar before you go.

For families, Winchester revolves around Jim Barnett Park for playgrounds, pools and ball fields, Handley Library for weekly baby and toddler programs, and the Shenandoah Valley Discovery Museum in Old Town for rainy days.

Who to call

Playgrounds and parks

  • Christianson Familyland, Jim Barnett Park, 1028 Lowry Drive. An adventure playground and an accessible playground, with parking and public restrooms close by, on the Green Circle Trail (Green Circle Trail page). The city held a free Playground Pop-Up here on July 30, 2026, with music, face painting, crafts and a sidewalk chalk contest (park events).
  • The rest of Jim Barnett Park, 1001 E. Cork St.: a paved walking trail with a story walk, a fishing lake, a BMX track, disc golf and picnic pavilions (Jim Barnett Park).
  • Whittier Park, 900 Whittier Ave.: a playground, a small picnic pavilion and large play fields, but no restrooms (Green Circle Trail page).
  • Neighborhood parks: the city lists Frederick Douglass, Friendship, Harvest Ridge, Park Place, Poles, Timbrook, Weaver and other parks; see our parks and trails guide.
  • The Trails at the MSV, 901 Amherst St.: a free art park with a treehouse, a stone circle and grassy “picnic mounds” 10 to 15 feet high, and 3 miles of trails that take strollers, open daily 7 a.m. to dusk (MSV trails page).

City parks are open dawn to dusk.

Library story times

Handley Library, 100 W. Piccadilly St., is open Monday to Thursday 10 a.m. to 8 p.m. and Friday and Saturday 10 a.m. to 5 p.m., closed Sunday. Its weekly programs for ages 0 to 5, as posted for October 2026 (Handley Library):

Day Program Time
Tuesday Baby Time 10:30 to 11 a.m.
Tuesday Family STEAM Lab 11 a.m. to noon
Wednesday Family STEAM Lab 11 a.m. to noon
Thursday Toddler Time 10:30 to 11 a.m.

The library has no parking lot of its own; use the metered street spaces or one of the downtown garages about a block away. Bowman Library in Stephens City runs its own baby and Lego programs (library events).

Rainy-day and indoor picks

  • Shenandoah Valley Discovery Museum, 19 W. Cork St. Four floors of hands-on exhibits for children 6 months to 10 years old and their families, plus summer camps (visitors bureau listing; museum).
  • Indoor pool, Jim Barnett Park. Open all year, with water at about 83 degrees and swim lessons year-round; children under 12 need an adult with them (city pools page).
  • Northside Lanes, 6 Richards Ave., 540-667-1470: bowling with a snack bar; open from noon Sunday and 9 a.m. Monday (Northside Lanes).
  • Go Play, 130 Windy Hill Lane: an indoor playground and bounce houses with a concession stand and coffee shop (visitors bureau listing).
  • Winchester Little Theatre, 315 W. Boscawen St.: “Theatre for Kids” shows each summer; in 2026 they were “The Three Musketeers” and “James and the Giant Peach” (2026 listing).

A drive away

  • Dinosaur Land, 3848 Stonewall Jackson Highway, White Post: a roadside park with more than 50 dinosaurs and other giant creatures, open since 1963; 9:30 a.m. to 5:30 p.m. from April 1 to Sept. 7, with last park admission at 4:30 p.m. (Dinosaur Land).
  • Marker-Miller Orchards, 3035 Cedar Creek Grade: wagon rides, a playground and pick-your-own fruit in season (visitors bureau listing). See our fall festivals and pumpkin patches guide.

Splash pad and summer

The Dancing Fountain splash pad on the Loudoun Street Mall is closed and is scheduled to reopen in summer 2027 (city project page). Pools and camps are in our summer camps and pools guide.

What this means for you

  • Library baby and toddler times run every week; check the calendar for changes.
  • Jim Barnett Park has the most for kids in one place, including restrooms.
  • On wet days, the Discovery Museum and the indoor pool are the Old Town and park standbys.

Related: free things to do, spring break and schools.

Frequently asked questions

When is story time at Handley Library in Winchester?

Handley Library, 100 W. Piccadilly St., runs Baby Time at 10:30 a.m. Tuesday and Toddler Time at 10:30 a.m. Thursday for ages 0 to 5, plus a Family STEAM Lab at 11 a.m. Tuesday and Wednesday, according to its October 2026 calendar.

Where is the best playground in Winchester, Virginia?

The main playground area is Christianson Familyland in Jim Barnett Park, 1028 Lowry Drive, which has both an adventure playground and an accessible playground, with parking and restrooms nearby.

What can kids do in Winchester when it rains?

The Shenandoah Valley Discovery Museum on West Cork Street has four floors of hands-on exhibits for children 6 months to 10 years old. Handley Library, the indoor pool at Jim Barnett Park, Northside Lanes bowling and the Go Play indoor playground are other indoor options.

Is the splash pad in Winchester open?

Not yet. The Dancing Fountain splash pad on the Loudoun Street Mall has been closed since its control system failed and is scheduled to reopen in summer 2027, the city says.