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Where to Valentine

Romantic Spots and Ideas is the go-to resource for shopping, dining, parks, events, and other helpful listings.

For Valentine’s Day, here are ten romantic locations for you and your special someone:

Westport Country Playhouse

Punctuate the night with an exclamation point! Get tickets to a play at this famous theatre and dazzle your partner with stunning stories and performances.


While you’re on a roll, visit MoCA for a dose of modern art and culture. Top it off with a cocktail at BarMoCA’s happy hour (Thursdays 5-7 p.m.) or peel away from the bar early and co-create your own masterpiece over a drink at Paint & Sip (Thursdays 5:45-7:15 p.m.).

The Cottage

Connect over a beautiful dinner and a glass of wine. Let renowned chef Brian Lewis and his team create a masterpiece for your date night. With exquisite culinary options, you’ll impress your date with your excellent taste in food and atmosphere.

Westport Astronomical Socieity

Align the stars at our observatory. Gaze at the beauty of our solar system with the one you love. The viewing experience, with the dome’s 12½ Newtonian Reflector (i.e. a huge telescope), is next to none.

Westport PAL Ice Rink

Bring your date for a skate before the season ends! Westport’s PAL Ice Rink is on the water next to the Longshore Marina. It’s a perfect place to embarrass yourself (or not!) and share a hot cocoa with your special someone afterwards. Hold hands and enjoy the cold winter breeze while gliding on ice.

Grace K. Salmon Park

Experience the serenity of Westport’s riverside park. Take a stroll in the beautiful park gardens, view the Saugatuck River, or sit and observe the gorgeous surroundings from one of their benches.

Imperial & Baker Avenues

Lux Bond & Green

Looking to up your gift-giving game? Lux Bond & Greencan provide you with amazing pieces of jewelry and sophisticated watches. Or if things are getting serious… you can pick up the special ring for your special someone.

Westport Library/Library of Things

Borrow the perfect romance novel and enjoy the season on your own, or share the experience with a partner.

Because books aren’t the only thing you can borrow here. Plan a cozy night in and borrow kitchen equipment to cook the perfect meal together, or a board game if you enjoy getting competitive. Puzzles, sports items, and other equipment are available to help make your night special.

Bridgewater Chocolate/Le Rouge Handmade Chocolates & Cakes by Aarti

Nothing speaks of desire quite like chocolate. Bridgewater and Aarti deliver the best treats to show your affection. Deliver a package of deliciously smooth chocolates to your Valentine to make their day a bit sweeter.

Blossom + Stem

What says “I love you” more than a beautiful bouquet of flowers? These floral experts can recommend and prepare an arrangement that dazzles their eyes as much as their heart. Whether classic roses or something out of the ordinary, they’ll make your Valentine bloom with joy.

  • Bar MoCA
  • Blossom + Stem
  • Bridgewater Chocolates
  • Grace K. Salmon Park
  • Lux, Bond & Green
  • PAL Ice Rink (Photo: Dawn Shmaruk)
  • Westport Astronomical
  • Westport Country Playhouse
  • Le Rouge by Aarti
  • The Cottage
  • Westport Library