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Date Spots in Connecticut for Valentine’s Day and Beyond

Coming up with a date idea is no easy feat – whether you’re planning a first date, third date, a big anniversary or something special with your girlfriends for Valentine’s Day. To ease the stress, we’ve put together a list of some of our favorite Connecticut date spots, broken down by what kind of date you’re planning.


Take a look below for our date suggestions – and if you’re still stumped, don’t hesitate to reach out to us onFacebook or Twitter to ask our social media team for help in planning your next date!

First Date
So you have the jitters, you’re a little nervous and you can’t figure out what to wear. Let’s face it, first dates can be intimidating, so it’s great to go out and do an activity together to help break the ice. Cork & Brew in Southington is the only place in Connecticut where you can make wine, beer and soda – you’re guaranteed to have a blast! Also check out City Steam Brewery Café in Hartford for more live comedy shows, great drinks and food.

Newly dating
You’ve been “official” for 31 days, 12 hours and 15 minutes – so now what? If you’re looking for something fun for Valentine’s Day weekend or any weekend – check out Hartford’s Black-Eyed Sally’s  for live jazz and blues music, Cajun cuisine and a southern juke joint atmosphere we know your significant other will love. Or, head to Mohegan Sun Casino or Foxwoods Resort Casino for a night jam-packed with entertainment – from clubbing, dining, concerts or fun at the slots and poker tables.

Special Date for Mom & Dad
When was the last time you went on a real date since becoming parents? Take a night off from being masters of the universe to enjoy each other. We recommend wine tasting at one of Connecticut’s beautiful vineyards. In Litchfield Hills County—try Sunset Meadows or Miranda Vineyards.  In New Haven county or the surrounding area, try Gouveia Vineyards and in New London explore the beautiful Maugle Sierra.  If you’re not up for wine tasting, how about heading to the theater? Take a look at performance calendars at The Bushnell or Hartford Stage to plan a fun night out on the town.

Anniversaries/Special Occasions
Celebrate your anniversary in a cozy Connecticut inn where you can escape the hustle and bustle of everyday life and just relax and unwind. For a resort retreat that has it all, seclude yourselves at the beautiful Water’s Edge Resort & Spa in Westbrook where you can enjoy the stunning shoreline views, delicious food and time at the spa – check out the resort’s popular package ”A Night to Remember” for a superior deal. For a romantic escape with some old-world charm, head to Griswold Inn and wander the historic town together, discover quaint antique stores and boutiques and dine at some of the best restaurants. For another historic bed-and-breakfast experience, head up to Litchfield Hills and stay at Old Riverton Inn – a colonial stagecoach inn since way back when.

Alternatively, how about making a dinner reservation at a restaurant you’ve always wanted to go to? Assagio in Branford is the epitome of contemporary and stylish northern Italy. The pasta, seafood crepes and wine list will leave you wanting more—and more you will have! Your adventure will be complete with a carriage or sleigh ride atAllegra Farms. A taste of the New England country side and touch of romance will make your special occasion one that you will never forget!

Girlfriend Dates
With friends like yours who needs a date? Grab your besties on Valentine’s Day – or any other day for that matter – for a fabulous day starting at Norwalk’s Chocopologie, where no one will be counting calories. Once you’ve indulged in your favorite pastries, head to the shops at Greenwich Avenue so the real fun can begin!  Now after all that hard work, relax and rejuvenate at the Born of Earth Spa.

Who’s up for yoga in the vineyards? Sounds amazing right? Hopkins Vineyards offers a one hour yoga class followed by wine, cheese and fruit for private groups. Take time to stroll around Litchfield’s boutique shops en route to Rock Hall Luxe Lodging.  Splurge a little (you’re so worth it!) and book their special Winter Bliss Special package including massages and a signature cocktail shaker.

Have fun ladies!

CT Travel