Labor Day 2027 in Winchester is Sept. 6. The Patsy Cline Block Party, the outdoor pool's last weekend, trash running a day late and free meters.

Last checked Oct. 19, 2026. This page is updated each year at the same address. The 2027 Labor Day plans had not been announced, so dated events below are from 2026 and marked that way.

Labor Day is Monday, Sept. 6, 2027. In Winchester the long weekend brings the Patsy Cline Block Party on Kent Street, the last swims of the season at the Jim Barnett Park outdoor pool and the start of apple season at the farm markets outside town. Trash pickup runs a day late that week.

Who to call

  • Trash and recycling: City of Winchester, 540-667-1815, holiday schedule
  • Pools: Winchester Parks and Recreation, 540-662-4946
  • Area events calendar: visitors bureau, 540-542-1326

Trash, parking and city services

From the city’s 2026 holiday collection schedule; the 2027 schedule had not been posted:

  • No trash or recycling service on Labor Day.
  • Monday to Thursday service runs one day late that week.
  • Yard waste collection is canceled.

Downtown parking meters are free on Labor Day, one of the city’s meter holidays (city parking page). The city’s HIVE after-school program was closed on Labor Day 2026 (childcare page). Our trash and recycling guide has your pickup day.

Patsy Cline Block Party

The Patsy Cline Historic House, 608 S. Kent St., hosts an old-fashioned block party every year on the Saturday of Labor Day weekend to celebrate her birthday, with live music from local and regional musicians playing Patsy Cline and country songs, according to organizer Celebrating Patsy Cline Inc. The 16th annual party was Saturday, Sept. 5, 2026, from 11 a.m. to 5 p.m., with free admission, and in 2026 it spread into the new Patsy Cline Memorial Park (2026 listing). The 2027 date had not been announced.

The house is open for tours Wednesday through Saturday from 10 a.m. to 4 p.m. and Sunday from 1 to 4 p.m. in season (Patsy Cline Historic House).

The pool’s last weekend

The outdoor pool at Jim Barnett Park, 1001 E. Cork St., is open from Memorial Day weekend through Labor Day weekend, the city says, so Labor Day weekend is the last chance for the 50-meter pool, the diving well and the 30-foot tube slide (city pools page). The indoor pool stays open all year. See our summer camps and pools guide.

More from Labor Day weekend 2026

  • Hungry for History, Aug. 28 to Sept. 7, 2026: museums and historic sites in Winchester, Frederick County and Clarke County ran food-themed programs, tastings and cooking demonstrations through Labor Day, organized by the visitors bureau (event program).
  • Honeycrisp Festival, Marker-Miller Orchards, 3035 Cedar Creek Grade: the farm market’s first Honeycrisp festival, Saturday, Sept. 5, 2026, 9 a.m. to 5 p.m., with live music from 1 to 4 p.m. and wagon rides (2026 listing; Marker-Miller festivals).
  • Colonial Costume and Dance, Winchester-Frederick County Visitors Center, 1400 S. Pleasant Valley Road: free presentations at 11 a.m. and 1 p.m. Sunday, Sept. 6, 2026 (2026 listing).
  • Dusk to Dawn Movie Marathon, Historic Route 11 Drive-In, 5890 Valley Pike, Stephens City: Friday and Saturday, Sept. 4-5, 2026 (2026 listing).
  • First Friday, Loudoun Street Mall: Friends of Old Town’s monthly evening, Sept. 4, 2026, from 5 p.m. (2026 listing).

Apple season follows: see our fall festivals and pumpkin patches guide.

What this means for you

  • If your trash day is Monday to Thursday, plan on pickup one day late Labor Day week.
  • Go to the Patsy Cline Block Party on the Saturday; it is free.
  • Swim while you can: the outdoor pool closes for the year after Labor Day weekend.

Related: Memorial Day, history and landmarks and free things to do in Winchester.

Frequently asked questions

When is Labor Day 2027?

Labor Day is Monday, Sept. 6, 2027.

Is there trash pickup on Labor Day in Winchester?

On Labor Day 2026 the city collected no trash or recycling, Monday to Thursday routes ran one day late and yard waste was canceled. The 2027 holiday schedule had not been posted.

When is the Patsy Cline Block Party?

Organizers hold it every year on the Saturday of Labor Day weekend at the Patsy Cline Historic House, 608 S. Kent St. The 16th annual party was Sept. 5, 2026, from 11 a.m. to 5 p.m., with free admission.

Is the Jim Barnett Park pool open on Labor Day?

The city says the outdoor pool at Jim Barnett Park is open from Memorial Day weekend through Labor Day weekend, so Labor Day weekend is the last of the outdoor season.

Are Winchester parking meters free on Labor Day?

Yes. Labor Day is one of the city’s free-parking holidays at downtown meters.