Valentine's Day 2027 in Winchester falls on a Sunday. Old Town's Chocolate Escape, Galentine's nights, a Valentine's brunch and date ideas, with last year's dates.
Last checked Oct. 19, 2026. This page is updated each year at the same address. No 2027 Valentine’s events had been announced yet, so the dates below are from February 2026 and are marked that way. We list dinners and events only when the venue announces them, and we will add 2027 plans as they are posted.
Valentine’s Day 2027 is Sunday, Feb. 14, so watch for events across the weekend of Feb. 12-14. Most of Winchester’s Valentine’s events happen in Old Town, on and around the Loudoun Street Mall, with brunches and wine nights at farms and wineries in Frederick County.
Plan ahead
- Old Town events: Friends of Old Town calendar
- Area calendar: Winchester-Frederick County visitors bureau, 540-542-1326
- Downtown parking: meters are free on weekends; Winchester Parking Authority, 540-722-7575
Last year’s events at a glance (2026)
| Date (2026) | Event | Where |
|---|---|---|
| Jan. 26 to Feb. 8 | FredCo Eats Restaurant Week | Frederick County restaurants |
| Saturday, Feb. 7 | Chocolate Escape, 2 to 5 p.m. | Old Town |
| Thursday, Feb. 12 | Galentine’s Night, 6 to 9 p.m. | Vibrissa, 10 N. Kent St. |
| Friday, Feb. 13 | Couples Therapy comedy show, 8 p.m. | Bright Box, 15 N. Loudoun St. |
| Friday, Feb. 13 | Galentine’s Paint and Sip, 6 p.m. | West Oaks Farm Market |
| Feb. 14-15 | Valentine’s and Galentine’s Brunch, 11 a.m. to 3 p.m. | Patti’s Place |
| Saturday, Feb. 14 | “Love Letters” with dessert, 7 p.m. | James Charles Winery |
| Feb. 23 to March 1 | Winchester Restaurant Week | Old Town |
Chocolate Escape in Old Town
Friends of Old Town’s annual Chocolate Escape was Saturday, Feb. 7, 2026, from 2 to 5 p.m.: a stroll through downtown sampling chocolate creations at participating restaurants and shops, with an official map released before the day (2026 listing). Watch the Friends of Old Town events page for the 2027 date.
Dinners and brunch
- Patti’s Place, 3178 Laurel Grove Road, at Laurel Grove Wine Farm, served a Valentine’s and Galentine’s brunch Saturday and Sunday, Feb. 14-15, 2026, from 11 a.m. to 3 p.m., with a seasonal menu and a glass of cava (2026 listing; Patti’s Place).
- Winchester Restaurant Week, Feb. 23 to March 1, 2026, brought limited-time menus at local restaurants; more than 30 took part the year before (restaurant week site).
- FredCo Eats Restaurant Week, Jan. 26 to Feb. 8, 2026, featured multi-course menus at Frederick County restaurants (FredCo Eats).
For year-round dinner ideas, see our date night guide and our brunch guide.
Galentine’s nights (2026)
- Galentine’s Night at Vibrissa, 10 N. Kent St., Thursday, Feb. 12, 6 to 9 p.m.: a flower bar, permanent jewelry, a photo booth and a DJ (2026 listing).
- Galentine’s Night Out at the Youth Development Center, Thursday, Feb. 12, 6 to 8 p.m. (2026 listing).
- Galentine’s Paint and Sip at West Oaks Farm Market, 4305 Middle Road, Friday, Feb. 13, at 6 p.m.: paint a champagne glass at your own pace (2026 listing).
Shows and wine (2026)
- “Love Letters” at James Charles Winery, 4063 Middle Road, Saturday, Feb. 14: doors at 7 p.m., the Selah Theatre Project’s performance at 7:30, with a chocolate fountain dessert (2026 listing).
- Couples Therapy: A Comedy Show at Bright Box, 15 N. Loudoun St., Friday, Feb. 13, at 8 p.m. (2026 listing).
- Love in a Heartbeat, a speed dating night at the Wayside Inn, 7783 Main St., Middletown, Thursday, Feb. 12, at 5 p.m. (2026 listing).
Date ideas any February weekend
- Walk the Loudoun Street Mall and the side streets of Old Town; our Old Town Winchester guide maps the blocks.
- See a show at the Winchester Little Theatre or Bright Box; see our live music and nightlife guide.
- Take a winter walk on the trails at the Museum of the Shenandoah Valley, open daily 7 a.m. to dusk (MSV); more in our walking and biking trails guide.
What this means for you
- With Feb. 14 on a Sunday in 2027, Valentine’s events may fall on Friday or Saturday, Feb. 12-13, as well as the day itself.
- Buy tickets ahead for ticketed brunches, shows and wine events.
- Check back in January, when venues post their 2027 plans.
Related: free things to do and things to do this month.
Frequently asked questions
What day is Valentine’s Day in 2027?
Valentine’s Day falls on Sunday, Feb. 14, 2027.
When is the Chocolate Escape in Old Town Winchester?
Friends of Old Town’s annual Chocolate Escape was Saturday, Feb. 7, 2026, from 2 to 5 p.m., with chocolate tastings at Old Town restaurants and shops. The 2027 date had not been posted on Oct. 19, 2026.
Where can I get Valentine’s brunch near Winchester?
In 2026 Patti’s Place, 3178 Laurel Grove Road, served a Valentine’s and Galentine’s brunch Feb. 14-15 from 11 a.m. to 3 p.m., with a glass of cava. Its 2027 plans had not been announced.
When is Winchester Restaurant Week?
Winchester Restaurant Week ran Feb. 23 to March 1, 2026, with limited-time menus at Old Town restaurants. FredCo Eats Restaurant Week, for Frederick County restaurants, ran Jan. 26 to Feb. 8, 2026.
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