Date night in Clarksville: Trattoria di Cat, Yada on Franklin, the Skyline 500 rooftop, the Roxy Regional Theatre, Beachaven winery and a comedy club.

Last checked Oct. 17, 2026. Every place on this page comes from its own website, linked below, with the hours it publishes. Hours change on holidays; check before you go. We do not rank restaurants or take payment for listings.

Clarksville’s best date nights are downtown, where dinner, a rooftop drink and a show are a short walk apart, and parking is free after 5 p.m. on weekdays and all weekend, according to the city’s parking page. For a slower afternoon, head to the winery or the distillery on the edge of town.

What this means for you

  • Dinner and a view: Trattoria di Cat, then upstairs to the Skyline 500 rooftop, both at Shelby’s Trio.
  • Small plates: Yada on Franklin; reservations online.
  • A show: the Roxy Regional Theatre’s season, or comedy on Fort Campbell Boulevard.
  • Daytime date: Beachaven’s tasting room or Old Glory’s Silo Park.

Dinner

Restaurant Address Dinner hours Phone
Trattoria di Cat at Shelby’s Trio 304 N. Second St. (second floor) 4 to 10 p.m. Thu.-Sun. 931-919-3373
Yada on Franklin 111 Franklin St. 4 to 9 p.m. Tue.-Wed.; 4 to 10 p.m. Thu.-Fri.; 2 to 10 p.m. Sat.; closed Sun.-Mon. 931-919-9232
The Mailroom 116 N. Second St. Until 10 p.m. Mon.-Thu. and Sun.; 11 p.m. Fri.-Sat. 931-919-5020
Strawberry Alley Ale Works 103 Strawberry Alley Until 10 p.m. Mon.-Thu. and Sun.; 11 p.m. Fri.-Sat. 931-919-4777

Trattoria di Cat is the Italian steakhouse on the second floor of Shelby’s Trio, named for Cathi Maynard, whose dream the restaurant was, with pastas, risottos, steaks from C. Blackwell Cattle Co. and large-format steaks for two. Reservations are taken online through the restaurant.

Yada on Franklin calls itself a fun, casual place to eat, drink and gather; its kitchen closes an hour before the listed closing time and the bar stays open until close. Reservations are online.

Drinks with a view

Skyline 500, the rooftop bar at Shelby’s Trio, overlooks downtown: 4 to 10 p.m. Tuesday to Thursday, 4 to 11 p.m. Friday, 3 to 11 p.m. Saturday and 3 to 10 p.m. Sunday, with happy hour 3 to 5 p.m. and late-night specials 8:30 to 10 p.m. Tuesday to Friday. On Songwriters on Skyline nights, hit songwriters play an acoustic set; doors open at 6 p.m. (Songwriters on Skyline). Shelby’s Trio has free parking for guests behind the restaurant and across Second Street.

A show

  • Roxy Regional Theatre, 114 Public Square (its temporary home): musicals and plays through the season, including A 1940s Radio Christmas Carol in December 2026 and Peter and the Starcatcher in February 2027. Box office 931-645-7699 (Roxy).
  • Candlelight concerts at the Wilma Rudolph Event Center, 1188 Cumberland Drive in Liberty Park: string quartets play by candlelight; upcoming dates are on Fever’s Clarksville page.
  • Joker’s Comedy House, 2150 Fort Campbell Blvd., Suite A: touring comedians and an open mic (calendar).
  • F&M Bank Arena, 101 Main St.: concerts and touring shows (arena).

Wine and spirits

  • Beachaven Vineyards & Winery, 1100 Dunlop Lane: tastings and tours, live music on summer weekends and the long-running Jazz on the Lawn; call 931-645-8867 for tour times (Beachaven).
  • Old Glory Distilling Co., 451 Alfred Thun Road: guided distillery tours and tastings, a restaurant and cocktails in the outdoor Silo Park, with live music on Fridays and Saturdays (Old Glory).

Free date ideas

A sunset walk on the Cumberland Riverwalk at McGregor Park, the First Thursday ArtWalk on Franklin Street, or the lights of Christmas on the Cumberland from Nov. 21 to Jan. 2. More on our free things to do page.

More: brunch, live music and nightlife, Valentine’s Day and downtown Clarksville.

Frequently asked questions

Where should I go for date night in Clarksville, Tennessee?

Downtown has the most choice within a short walk: Trattoria di Cat and the Skyline 500 rooftop at Shelby’s Trio, Yada on Franklin, The Mailroom and a show at the Roxy Regional Theatre. Parking downtown is free after 5 p.m. on weekdays and all weekend.

What are Trattoria di Cat’s hours?

The Italian steakhouse on the second floor of Shelby’s Trio, 304 N. Second St., is open 4 to 10 p.m. Thursday through Sunday. Reservations are taken online; call 931-919-3373.

Is there a winery near Clarksville?

Beachaven Vineyards & Winery is in Clarksville at 1100 Dunlop Lane, with tastings and live music on summer weekends. Call 931-645-8867.

What is open late in downtown Clarksville?

On Fridays and Saturdays, Shelby’s Trio’s Skyline 500 rooftop, Strawberry Alley Ale Works and The Mailroom stay open until 11 p.m., according to their websites.