Father's Day 2027 in Winchester is June 20, the day after Juneteenth. Car shows, weekend brunch, breweries, ballgames and last year's events.

Last checked Oct. 19, 2026. This page is updated each year at the same address. No 2027 Father’s Day events had been announced, so dated events below are from 2025 and 2026 and marked that way. We list a Father’s Day special only when the venue announces it.

Father’s Day is Sunday, June 20, 2027, the day after Juneteenth (Saturday, June 19). In Winchester the weekend usually means a car show, a brewery or cidery in Old Town, brunch and the first weeks of the summer baseball and pool season.

Plan ahead

Car shows

  • Father’s Day Car and Truck Show (2025), Middletown Community Park, Senseney Avenue and Second Street, Middletown: the Hot Rod Cruisers’ show on Sunday, June 15, 2025, from 9 a.m. to 3 p.m., open to all model years, with an oldies DJ, a food vendor and participants’ choice awards (2025 listing). No 2026 show was listed.
  • Apple Blossom Antique Car Show, Jim Barnett Park: the Shenandoah Region AACA’s 66th annual meet was Saturday, May 9, 2026, free and open to cars, trucks and motorcycles 2001 and older (2026 listing; Shenandoah Region AACA).
  • Middletown’s Annual Car, Truck and Tractor Show: Saturday, Aug. 15, 2026, 3 to 8 p.m. (2026 listing).
  • Winchester Police Department Car Show, Old Town: Sunday, Sept. 13, 2026, noon to 4 p.m. (2026 listing).

Father’s Day weekend in 2026

What was on in Winchester the weekend of June 19-21, 2026, as a guide to what to expect:

  • Juneteenth Celebration, Loudoun Street Mall on the lawn of the Shenandoah Valley Civil War Museum: Hood-Love’s fifth annual free evening of speakers, vendors, food trucks, live music and kids’ activities, Friday, June 19, 3 to 9 p.m. Bring lawn chairs (2026 listing).
  • Litha Luna Market, in front of Moon Phased, 125 S. Loudoun St.: more than 20 vendors on the walking mall, Saturday, June 20, 10 a.m. to 5 p.m. (2026 listing).
  • Quilt Discovery Day, Museum of the Shenandoah Valley, 901 Amherst St.: a quilt expert examined family quilts in 20-minute sessions, Saturday, June 20 (2026 listing).

Brunch for Dad

These places serve brunch every weekend, according to their own websites:

  • Union Jack Pub and Restaurant, 101 N. Loudoun St., in the historic Union Bank Building: brunch Saturday and Sunday, 10 a.m. to 4 p.m., including an English breakfast (brunch menu).
  • Bonnie Blue Southern Market and Bakery, 334 W. Boscawen St., in a converted 1920s gas station: weekend brunch, open 8 a.m. to 4 p.m. Saturday and Sunday (Bonnie Blue).
  • Bistro SOJO, 12 S. Braddock St.: Sunday brunch, 10:30 a.m. to 3 p.m. (Bistro SOJO).

More places in our brunch guide.

Breweries, cider and a ballgame

Old Town has several small breweries within a few blocks of the walking mall, listed by the visitors bureau:

The Winchester Royals play summer baseball at Bridgeforth Field in Jim Barnett Park; the team posts its schedule at winchesterroyals.org. The Jim Barnett Park outdoor pool is open by Father’s Day; see our summer camps and pools guide.

What this means for you

  • Check back in May, when venues post Father’s Day 2027 plans; we add them here.
  • Brunch places in Old Town do not all take reservations; Paladin Downtown, for one, seats first come, first served.
  • Parking downtown is free all weekend.

Related: Mother’s Day, live music and nightlife and date night in Winchester.

Frequently asked questions

When is Father’s Day 2027?

Father’s Day is Sunday, June 20, 2027. Juneteenth falls the day before, on Saturday, June 19.

Is there a Father’s Day car show near Winchester?

The Hot Rod Cruisers held a Father’s Day Car and Truck Show at Middletown Community Park on June 15, 2025, from 9 a.m. to 3 p.m. No 2026 or 2027 show had been listed when we checked.

Where can I take Dad for brunch in Winchester on Father’s Day?

Union Jack Pub serves brunch Saturday and Sunday from 10 a.m. to 4 p.m., Bonnie Blue Southern Market and Bakery has a weekend brunch menu, and Bistro SOJO serves Sunday brunch from 10:30 a.m. to 3 p.m., according to their own sites.

Are Winchester parking meters free on Father’s Day?

Yes. Father’s Day is a Sunday, and downtown meters are free on weekends and on Juneteenth, according to the city’s parking page.