Date night in Clermont: dinner, wine, shows and late spots

Last checked Oct. 8, 2026. Every hour, address and detail comes from the venue’s own website, Clermont Main Street’s downtown directory or the City of Clermont, linked. We list places; we do not rank them or list prices. Hours change, so check before you go.

A Clermont date night usually starts downtown, where restaurants, two breweries and a wine shop sit within a few blocks of Montrose Street and the sunset view over Lake Minneola. For a show, the city’s Clermont Performing Arts Center on U.S. 27 runs a season of concerts and comedy. And once a month, Main Street turns downtown into a wine walk.

Good to know

• On the water: Salt Shack on the Lake, 846 W. Osceola St.
• Show night: Clermont Performing Arts Center, box office 352-394-4800
• Late: The Roasted Spirit, open to 2 a.m. Friday and Saturday
• Parking: free downtown, more than 1,000 public spaces

Dinner downtown

Addresses for Crafted Steakhouse, Cosa Nostra and Pepe’s Cantina are from Clermont Main Street’s directory. More restaurants: a guide to historic downtown Clermont.

Wine

• Back 40 Wine Co., 719 West Ave., downtown.
• The monthly Wine Stroll, 6:30 to 9 p.m., with samples of more than 25 wines at about 25 downtown businesses. Ticketed, with check-in at 756 W. Montrose St. Coming up: Sat. Oct. 17, Friday, Nov. 13, and Friday, Dec. 18, 2026.
• Lakeridge Winery & Vineyards, 19239 U.S. Highway 27 north of town, listed by the state’s agritourism program. Phone: 352-394-8627.
• Southern Hill Farms, 16651 Schofield Road, held evening Wine Walks and Farmer’s Harvest Dinners in spring 2026; watch its calendar for the next season.

Shows

The Clermont Performing Arts Center, 3700 S. U.S. Highway 27, runs tribute concerts, comedy nights and holiday shows, with tickets sold online and through the box office, 352-394-4800. The 2026-27 line-up is on its website; its big band Christmas show, Home for the Holidays, is Sat. Dec. 5 at 7 p.m.

Before or after dinner

• Sunset by the lake. Waterfront Park and Victory Pointe sit at the foot of downtown on Lake Minneola; city parks close at dusk.
• The Citrus Tower. The Florida Citrus Tower, 141 N. U.S. Highway 27, opened in 1956 and takes visitors by elevator to an observation deck with views the tower puts at 35 miles. It has a coffee shop and hosts weddings and events. Phone: 352-394-4061.
• Breweries. Clermont Brewing Company, 750 W. DeSoto St., and Suncreek Brewery, 790 W. Minneola Ave., two blocks apart. See live music and nightlife.
• Holiday lights. From Nov. 21 to Jan. 2 the Enchanted Forest of Trees lights up Victory Pointe; see holiday lights and Christmas events.

Seasonal date nights

Valentine’s Day, New Year’s Eve and holiday plans are on their own pages: Valentine’s Day, New Year’s Eve. Restaurants with a special menu or event can tell the newsroom.

Frequently asked questions

Where can you eat on the water in Clermont?

Salt Shack on the Lake, 846 W. Osceola St. in historic downtown, serves wild-caught seafood and craft cocktails on Lake Minneola. Phone: 352-562-7840.

What is there to do at night in Clermont?

Downtown has two breweries, bars open as late as 2 a.m. on weekends and a monthly Wine Stroll; the Clermont Performing Arts Center on U.S. 27 stages concerts, comedy and holiday shows.

Is there a winery in Clermont?

Lakeridge Winery & Vineyards is at 19239 U.S. Highway 27 north of town, according to the state’s agritourism listing. Phone: 352-394-8627.

When is the next Clermont Wine Stroll?

Clermont Main Street’s Wine Stroll runs 6:30 to 9 p.m. on Sat. Oct. 17, Friday, Nov. 13, and Friday, Dec. 18, 2026, with check-in at 756 W. Montrose St. Tickets are required for tasting.