Valentine's Day 2027 is a Sunday. What Cary held last year, from a free date night in Downtown Cary Park to Valentine's concerts, and when to look for 2027.

Last checked Oct. 11, 2026. This page is updated each year at the same address. Facts come from each organizer’s own page, linked below. Restaurant specials appear here only when the restaurant announces them.

Valentine’s Day 2027 is Sunday, Feb. 14. Cary venues usually post their Valentine’s events in January, so the 2027 dates are not out yet. Here is what ran in February 2026, so you know what to look for. Each date below is from 2026; we will replace them with 2027 dates as organizers post them.

Who to call

  • Town events and the Cary Arts Center: Cary 311, or 919-469-4000 from outside town limits
  • Tickets for town concerts and The Cary Theater: Cary Box Office, 122 E. Chatham St.
  • Emergency: 911

What ran in 2026

2026 date Event Time Place
Wednesday, Feb. 11 High Seas Hijinks: a mom and son pirate adventure 6 p.m. Bond Park
Saturday, Feb. 14 Valentine’s Date Night in the Park (free, ages 16+) 5 to 9 p.m. Downtown Cary Park
Saturday, Feb. 14 A Valentine’s Night of Jazz, R&B and Funk with Chip Shearin 7:30 p.m. Cary Arts Center
Saturday, Feb. 14 Sisters in Song 7:30 p.m. The Cary Theater

Valentine’s Date Night in the Park. A free evening for couples 16 and up in the Academy Pavilion and Gathering House at Downtown Cary Park. In 2026 it ran 5 to 9 p.m. on Feb. 14, with hands-on activities first come, first served: Jane Austen-style folded love letters sealed with wax, Valentine’s terrarium kits, a Polaroid photo wall and a painted-heart Love Note Project, plus live music from the Josh Colton Duo and a food truck (2026 event page).

The town’s Valentine’s concert at the Cary Arts Center, 101 Dry Ave. In 2026 it was A Valentine’s Night of Jazz, R&B and Funk with bassist Chip Shearin at 7:30 p.m. Feb. 14, according to the town’s January 2026 newsletter. In 2025 the town paired Chip Shearin with trumpeter Al Strong for a neo-soul jazz night, listed on its Valentine’s weekend page. Tickets go through Etix and the Cary Box Office.

Sisters in Song at The Cary Theater, 122 E. Chatham St. Carrie Marshall, Lydia Salett Dudley and Persona Bell sang songs by Nina Simone, Alicia Keys, Roberta Flack, Carole King and others at 7:30 p.m. Feb. 14, 2026. The theater posts its season on its calendar.

For moms and sons. The town’s High Seas Hijinks pirate night at Bond Park on Feb. 11, 2026, had a battleship game, a treasure hunt, a pirate feast and s’mores, with registration for each person through the town’s RecTrac system.

Date ideas that do not depend on the calendar

Valentine’s dinners

No Cary restaurant had posted a 2027 Valentine’s menu as of Oct. 11. Restaurants usually announce them in January. We will list them here, linked to each restaurant’s own page, as they appear. Brunch the next morning? See our brunch guide.

What this means for you

  • Watch for 2027 dates in early January: the free date night in the park fills on a first come, first served basis.
  • Town concert tickets sell through Etix and the Cary Box Office.

Frequently asked questions

When is Valentine’s Day 2027?

Valentine’s Day 2027 falls on Sunday, Feb. 14.

Is there a free Valentine’s event in Cary?

In 2026 Downtown Cary Park held a free Valentine’s Date Night in the Park for couples 16 and up, 5 to 9 p.m. Feb. 14. The 2027 date had not been posted when we checked.

Where is the Valentine’s concert in Cary?

The town’s Valentine’s concert is at the Cary Arts Center, 101 Dry Ave. In 2026 it was A Valentine’s Night of Jazz, R&B and Funk with Chip Shearin at 7:30 p.m. Feb. 14.

Where can I find Valentine’s dinners in Cary?

We list Valentine’s menus only when a restaurant posts one on its own site, usually in January. Until then, see our date night guide for restaurants and late openings.