Date night in Leesburg, from venues' own sites: dinner at Lightfoot, Tuscarora Mill or Shutters' rooftop, Tally Ho shows, Oatlands evening events and late tables.

Last checked Oct. 20, 2026. Every detail comes from the venue’s own website, linked below; hours change, so check before you go. Listed by type, then alphabetically.

Leesburg’s date nights center on downtown, where a handful of independent restaurants, the Tally Ho Theater and two breweries sit within a few blocks of King and Market streets, and on Oatlands south of town, which opens its mansion and Carriage House for evening tours, dinner theater and candlelight nights. Weekend and evening parking in the downtown garages is free. For the Tally Ho, call 703-777-1665.

Who to call

  • Lightfoot: 703-771-2233
  • Shutters on King: 703-936-4700
  • Tuscarora Mill: 703-771-9300
  • Tally Ho Theater: 703-777-1665

Dinner

Restaurant Address Why for a date Hours (from the restaurant)
Lightfoot 11 N. King St. “Inspired American cuisine”; bar happy hour Opens 11:30 a.m. Wednesday to Sunday
Shoe’s Cup & Cork 17 N. King St. Brasserie with a garden courtyard, the Secret Garden Dinner 5 to 9 p.m. Monday and Thursday, to 10 p.m. Friday and Saturday; closed Tuesday and Wednesday
Shutters on King 102 S. King St. Three levels, main bar and rooftop patio 11 a.m. to 10 p.m. Monday to Thursday, to midnight Friday and Saturday; Sunday dinner from 3 p.m.
The Conche 1605 Village Market Blvd. SE Menu built around its own chocolate lab Reservations online; 703-779-1800
Tuscarora Mill 203 Harrison St. SE At Market Station, with a late evening menu 11 a.m. to 10 p.m. Monday to Thursday, to 11 p.m. Friday and Saturday; 10 a.m. to 9 p.m. Sunday

Book ahead for Friday and Saturday: Lightfoot, The Conche and Tuscarora Mill take reservations on their sites, and Tuscarora Mill asks parties of six or more to call.

A show

  • Tally Ho Theater, 19 W. Market St. Concerts, tribute bands and Comedy Night in Leesburg presented by the DC Improv. Tickets through the theater’s site; doors usually open at 7 p.m.
  • Phoenix Theatres, Village at Leesburg. The center’s events page lists $5 Bargain Tuesdays.
  • Dinner theater at Oatlands. StageCoach Theatre Company staged Spies and Cyanide, an immersive dinner-theater mystery set in 1779 around the Culper Spy Ring, in the Oatlands Carriage House on June 28 and Aug. 22, 2026 (Oatlands).

Evenings at Oatlands

Oatlands, 20850 Oatlands Plantation Lane, runs after-hours events through the year:

  • Twilight Tours, about an hour of overlooked spaces and hidden histories after closing time; the next is Spooky Stories, 6:30 p.m. Sunday, Oct. 25 (tickets). In summer 2026 they included Twilight Garden Tours.
  • Candlelight Nights, 5 to 7 p.m. Dec. 19 and 20, with the decorated mansion lit by candles, live music, and cider and cookies in the greenhouse (Dec. 19).
  • Garden Soiree, an afternoon of seasonal cocktails, hors d’oeuvres and lawn games, held Sept. 20 in 2026.

Drinks and late tables

  • Shutters on King stays open until midnight on Friday and Saturday, with a rooftop patio.
  • Loudoun Brewing Company, 310 E. Market St., and Dynasty Brewing, 101 Loudoun St. SE, pour downtown; hours and details are in our live music and nightlife guide.
  • Kilwins, 17 S. King St., for chocolates and ice cream after dinner (town release).

Daytime dates

Walk Morven Park’s free boxwood gardens and grounds (7 a.m. to 6 p.m. daily) or the W&OD Trail, then brunch downtown; see our brunch guide and free things to do.

What this means for you

For a Friday or Saturday, reserve dinner first, then pick a Tally Ho show or a late table at Shutters. Watch the Oatlands calendar for Twilight Tours and December’s Candlelight Nights, which sell by the ticket. Park free in the Town Hall Garage after 7 p.m. and walk. For seasonal plans, see Valentine’s Day and New Year’s Eve.

Frequently asked questions

Where should I go for a date night dinner in Leesburg?

Downtown options include Lightfoot at 11 N. King St., Shutters on King at 102 S. King St. with its rooftop patio, Tuscarora Mill at 203 Harrison St. SE and Shoe’s Cup & Cork at 17 N. King St. with its garden courtyard. The Conche is at the Village at Leesburg.

What restaurants are open late in Leesburg?

Shutters on King is open until midnight Friday and Saturday, Tuscarora Mill until 11 p.m. Friday and Saturday, and Shoe’s Cup & Cork serves dinner until 10 p.m. Friday and Saturday.

Is there a theater in Leesburg?

The Tally Ho Theater at 19 W. Market St. books concerts, tribute bands and comedy. Oatlands has hosted StageCoach Theatre’s dinner theater in its Carriage House.

Are there evening events at Oatlands?

Yes. Oatlands runs Twilight Tours after hours through the year, including Spooky Stories on Oct. 25, 2026, and Candlelight Nights on Dec. 19 and 20, 2026, from 5 to 7 p.m.