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Ten Summer Date Ideas

Creative date ideas in New Canaan, Darien, Rowayton and more


1. Up for an adventure on Five Mile River? Try yoga on a Stand Up Paddleboard. Darien’s Danielle Brown will have you saluting the sun while balancing on the water, contact her if you want to arrange a semi-private, or attend a class Wednesdays or Fridays at 5 pm. Afterwards, stroll just down the street for a civilized dinner, food is now being served on the deck at Rowayton Seafood (first come, first served so you may need to wait for a table).

2. Change things up, head to downtown Stamford and grab a bite from one of the many restaurants on Bedford Street, then check out what’s playing at the Avon Theater (catch summer classic Jaws on July 2) or head over to Columbus Park for the Alive @ Five concert series (The Beach Boys will close the season on August 14).

3. If you are in the mood to burn some calories while you spend quality time with your significant other you can pick up lunch at Rosie’s (27 Elm St) and go to Waveny for a picnic and hike on their beautiful trails. If you want to really impress your date, plan ahead and check out the Carriage Barn Arts Center, which is appointment during the summer (Monday and Tuesday only).

4. Eager to work up a sweat? Check out Venture Yoga’s summer schedule. They have evening classes on weeknights during the summer. You’ll need a shower and change of clothes before heading downstairs to Darien Social for a bite to eat, but you’ll know you’ve earned it.

5. Puppy love shouldn’t be scoffed at.  Take Spot along on your date, the dog park in Rowayton welcomes all comers and doesn’t require your pup to stay on a leash (36 McKinley St). You can walk from there to Flea (behind Sails) where the human contingent can enjoy homemade dark chocolate-covered peanut butter cups and a coffee.

6. Sunset is the perfect time for wine and cheese at Pear Tree Beach. Start off at Goodwives where Darien Cheese & Fine Foods will set you up with just the right thing.  If you can’t snag the good table at the beach, or the gazebo, rest assured there will be 2 Adirondak chairs with your names on them.

7. If you haven’t yet visited Philip Johnson’s Glass House, or even if you haven’t yet gone in the summer, make a reservation for the self-guided tour (a relatively new offering) and check out this magnificent property at your own pace.

8. Channel your inner nerds, see what’s on at the library. Darien Library is hosting everything from World Cup viewing parties to a Friday Night Feature Movie series. Best part? It’s all free, so you can spend your money on a fancy dinner afterwards.  

9. Speaking of a fancy dinner, if you care to travel farther afield, take your date to Stone Barns at Blue Hill. Purported by many to be the best restaurant in the area, you can also check out the Blue Hill Farm at its summer best.

10. Up for some silly fun? Test out your dates ability to wow a crowd, Fuji in Darien hosts a karaoke night every Friday starting at 9 pm.