Valentine's Day in Wesley Chapel 2027: dinners and date ideas

Last checked Oct. 10, 2026. This page is updated each year at the same address. Valentine’s menus and events are listed only when the venue announces them on its own page; as of this check, none had posted 2027 plans. Hours and details below come from each venue’s own site.

Valentine’s Day 2027 is Sunday, Feb. 14, and Presidents Day follows on Monday, Feb. 15, so many families have a long weekend. Wesley Chapel’s dinner reservations cluster at The Shops at Wiregrass and Saddlebrook Resort. Wiregrass center office: 813-994-2242. Saddlebrook: 813-973-1111.

Valentine’s weekend, 2027

• Friday, Feb. 12: a Pasco County Schools student day that becomes a day off if it is not needed to make up lost time
• Sunday, Feb. 14: Valentine’s Day
• Monday, Feb. 15: Presidents Day; no school, Pasco County libraries closed

Dinner: restaurants that take reservations

These restaurants book tables online. None had posted a 2027 Valentine’s menu when we checked.

• The Living Room describes itself as a chef-driven New American restaurant with a scratch kitchen, craft cocktails and live music, and lists weekend brunch.
• RARE 1981 is Saddlebrook’s newest restaurant, with Gulf Coast flavors and regionally sourced meats and seafood. It serves dinner Thursday through Sunday only; Saddlebrook offers free valet parking to diners.
• More restaurants, theaters and late openings are in our date night in Wesley Chapel guide, and weekend brunch spots for a Valentine’s Sunday brunch are on our brunch page.

Skating at AdventHealth Center Ice

The rink at 3173 Cypress Ridge Blvd. posts its public skate sessions on its events calendar. It runs themed skates during the year, such as its October Hallowrink. If it adds a Valentine’s skate, we will list it here. Call 813-803-7372.

A walk outdoors

• Flatwoods Park, run by Hillsborough County, has a 7-mile paved loop for walking and biking, with entrances at 14302 Morris Bridge Road and 18205 Bruce B. Downs Blvd. In fall and winter it is open 7 a.m. to 6 p.m.; there is a per-vehicle entry fee, and pets are allowed. County page
• The west side of Morris Bridge Conservation Park, on the Hillsborough River, is closed until further notice while the state clears river damage, the county says.

More trails are in our walking and biking trails guide.

Live music

The Brass Tap at Wiregrass, 2000 Piazza Ave., Unit 110, and The Living Room both list live music; schedules are on our live music and nightlife page.

What is closed on Presidents Day

• Pasco County libraries, including the New River Branch Library, are closed Monday, Feb. 15, 2027, the library system says.
• Pasco County Schools are closed Feb. 15 for Presidents Day; Feb. 12 becomes a day off only if it is not needed as a makeup day, the district calendar says.

What this means for you

• Book dinner as soon as reservations open for Feb. 14.
• RARE 1981 is closed for dinner Monday through Wednesday, so Sunday, Feb. 14, is the night.
• Have a Valentine’s event in Wesley Chapel? Send it to us.

Frequently asked questions

What day is Valentine’s Day 2027?

Sunday, Feb. 14, 2027. The next day, Monday, Feb. 15, is Presidents Day, when Pasco County Schools and libraries are closed.

Where can I book a Valentine’s dinner in Wesley Chapel?

Restaurants that take reservations include The Living Room and Grillsmith at The Shops at Wiregrass, and RARE 1981 at Saddlebrook Resort, which serves dinner from 5 to 9 p.m. on Sundays. Book early; we add Valentine’s menus as restaurants announce them.

Is there ice skating in Wesley Chapel?

Yes. AdventHealth Center Ice, 3173 Cypress Ridge Blvd., runs public skate sessions posted on its online calendar. Call 813-803-7372.

Are there Valentine’s events in Wesley Chapel?

None had been announced for 2027 when we checked in October 2026. We update this page as the town centers and venues post them.