Valentine's Day is Sunday, Feb. 14, 2027. The For the Love of Chocolate 5K runs that morning at Southern Hill Farms; more Clermont events are added as venues post them.

Last checked Oct. 8, 2026. This page is updated each year at the same address. Sources: Southern Hill Farms’ events, the race’s registration page, the City of Clermont’s event calendar and Clermont Main Street. We list only what venues announce; we do not list prices or rank restaurants.

Valentine’s Day 2027 falls on a Sunday, Feb. 14. It is early: only one Clermont event had a 2027 date when we checked, a chocolate-themed 5K at a farm in south Clermont. Below are last year’s events, labeled by year, so you know what to watch for, and a short list of date ideas that do not need a reservation.

Good to know

  • Confirmed for 2027: For the Love of Chocolate 5K, 8 a.m. Sunday, Feb. 14, Southern Hill Farms
  • Weekend before: Valentine’s falls on Sunday, so Friday, Feb. 12, and Saturday, Feb. 13, are the big dinner nights
  • Restaurants: we add Valentine’s menus only when a restaurant posts one

Confirmed for 2027

Dream Finders Homes For the Love of Chocolate 5K, Sunday, Feb. 14, 2027, 8 a.m. The race starts and finishes at Southern Hill Farms, 16651 Schofield Road, with kids races at 9:30 a.m. In 2026 finishers got sweet treats at the line, and the farm says to enter by Gate 4 from Schofield Road.

What happened in 2026

2026 date Event Where
Sat. Feb. 7 and Sun. Feb. 8 Love Your Local Farmer Weekend: food trucks and fun zone, 11 a.m. to 4 p.m. Southern Hill Farms
Friday, Feb. 13, 4 to 9 p.m. Valentine’s Date Night: sunflower fields until sunset, select carnival rides, a romantic movie on the lawn at 7 p.m., dinner from the farm’s pizzeria and burger truck (ticketed) Southern Hill Farms
Friday, Feb. 13, 7 to 9 p.m. Philharmonia Valentine’s Day concert Clermont Performing Arts Center
Sat. Feb. 21, 6:30 to 9 p.m. February Wine Stroll at 20-plus downtown businesses Starts at 756 W. Montrose St.

We will replace these with 2027 dates as each organizer posts them.

Dinner

No Clermont restaurant had posted a 2027 Valentine’s menu when we checked. When they do, we will list them here with a link to the restaurant’s own page. Until then, our date night guide lists downtown restaurants, wine bars and the Performing Arts Center, and our brunch guide covers Sunday morning.

Date ideas

  • Sunset on Lake Minneola. Waterfront Park and the paved Clermont/Minneola Trail run along the lakefront. City parks are open until dusk. See walking and biking trails.
  • The Citrus Tower. The Florida Citrus Tower, 141 N. U.S. Highway 27, takes visitors by elevator to an observation deck with views the tower puts at 35 miles. It has a coffee shop on site. Phone: 352-394-4061.
  • A winery tour. Lakeridge Winery & Vineyards is at 19239 U.S. Highway 27 north of town, according to the state’s agritourism listing. Phone: 352-394-8627.
  • A show. The Clermont Performing Arts Center, 3700 S. U.S. Highway 27, posts its winter line-up online; the box office is 352-394-4800.
  • Downtown. Historic downtown has breweries, a wine shop and restaurants within a few blocks of Montrose Street. Our guide to historic downtown Clermont has the map.

Planning a Valentine’s event in Clermont? Send it to the newsroom with a link to your page.

Frequently asked questions

What is happening in Clermont on Valentine’s Day 2027?

The Dream Finders Homes For the Love of Chocolate 5K starts at 8 a.m. Sunday, Feb. 14, 2027, at Southern Hill Farms. Other Valentine’s events are added to this page as venues announce them.

Does Southern Hill Farms do a Valentine’s event?

In 2026 the farm held a ticketed Valentine’s Date Night on Friday, Feb. 13, from 4 to 9 p.m., with sunflower fields, a movie on the lawn at 7 p.m. and dinner from its food trucks. The 2027 date is not out yet.

Is there a Valentine’s concert in Clermont?

In 2026 the Clermont Performing Arts Center hosted Philharmonia Valentine’s Day on Feb. 13 at 7 p.m. Its 2027 Valentine’s show had not been announced when we checked.

Where can couples go for a sunset in Clermont?

Waterfront Park and the Clermont/Minneola Trail run along the south shore of Lake Minneola, and city parks are open until dusk. The Citrus Tower’s observation deck looks out over the hills and lakes.