Unexpected Westport

The unexpected perfect romantic gesture

Whether you are a visitor, a resident or potential resident, DiscoverWestportCT.com is Westport’s go-to resource to find what you are looking for in Westport – from shopping and dining to parks, events and many other helpful listings.

With the month of romance coming to a start, we’ve picked some of the more unexpected events, locations and ideas for the perfect romantic gesture:

Westport PAL Rink at Longshore

Grab your skates and hop on the ice at Westport’s own public ice rink. With only a few weeks left to show off your skating skills, or lack thereof, you can skate with your date for an evening of pure bliss.

Eya Medieval Music @ CHT

On February 3rd, display your knowledge of culture by taking your date to a performance led by the award winning musical organization, Eya. A concert in honor of the 6th century patroness saint of Ireland, this performance will include beautifully crafted songs and harp strings strummed to serenity, all within the dimly lit radiance of candlelight.

Saturday Run @ Donut Crazy

Get your day started with a rush of adrenaline! Every Saturday, Westporters come together to run along a set path through some of Westport’s most well known locations. When the 6 to 12 mile route is over, enjoy some great conversations with other joggers at Donut Crazy.

An Evening with Audra McDonald @ Westport Country Playhouse

Named as one of Time magazine’s 100 most influential people, the winner of a record-breaking six Tony Awards, two Grammy Awards and an Emmy, Audra McDonald is visiting Westport Country Playhouse for an unbelievable event including songs from the golden age of Broadway.

Jazz with The Sherry Winston Band @ The Westport Library

Join the Sherry Winston Band for a night of jazz at the Westport Library. Sherry Winston has performed for two presidents, has played alongside Stevie Wonder, and she and her band of musicians are ready to perform for you and your date on February 11th.

Craft & Sip: Candle Making @ Earthplace

Enjoy a fun and stress-free activity with your special someone while sipping your favorite drinks. With the use of beeswax sheets, you can create multiple candles to use at home for your next romantic night in.

Live Music @ The Black Duck

Enjoy drinks, lights and tunes at Westport’s iconic bar and grill. The Black Duck hosts a variety of exciting bands and musicians throughout the year, including local favorites 9 of Hearts.

Chess Club for Adults @ The Westport Library

Want to compete against your date in a game of strategy? Join Westport Library’s Chess Club for Adults. With four meetings every month, you’ll always have time to learn, play and put your partner in checkmate!



Start your own book club, alongside your partner, with the help of WestportREADS’ book selection of 2024. Michael Finkel’s The Art Thief is the perfect novel to share and discuss what kept you turning the pages. When you’re done, experience WestportREADS’ film pairing, The Thomas Crown Affair, to discuss similar characters and themes between the two mediums. Check out panels and activity ideas related to The Art Thief at The Westport Library.

Into the Sanitarium Escape Room @ The Westport Museum

You’ve been trapped in a Sanitarium with your loved one and you have to find a way to escape! Use clues and puzzles around the room to try and find a way out before the staff comes back to run their tests. Reserve your spot for this fun and exciting adventure at the Westport Museum.

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