New Call-to-action
Destinations & Day Trips

12 Fun Date Night Ideas in CT That You Have to Try

Written by Ryan Sylvestre

Whether it’s for your first date with someone or for a regular “date night” with your long-term partner, finding the right date ideas can be stressful. Where should you go? What should you do? To make it easier, we’ve pulled together these suggestions for some of our favorite dates in CT.

Date night can be stressful. It’s your turn to pick the place and you used up your last great idea last week. You can’t let your partner down—but you’ve racked your brain for hours and just can’t think of anything fun, exciting, and new to try.

We feel you. Whether it’s for a first date, for Valentine’s Day, a special occasion like an anniversary or birthday, or just your run-of-the-mill date night, sometimes it can be hard to get a good idea rolling for the big night.

To help make things a little easier, we’ve taken the liberty of creating a list of fun and unique date ideas for the couple who has exhausted all other possibilities. These ideas are sure to take your date night to the next level and to keep the date train moving.

1. Stony creek Brewery—Branford


Stony creek brewery has been a popular craft brew house of the New Haven area for a while now. It’s very easy to get to because they are located walking distance from the Branford train station (making it even easier to drink responsibly if you don’t have to drive home afterward!). They offer some of the best beers and have a unique food truck there every night for a different food experience every time. (I highly recommend the hot dog truck.)

The inside has a modern rustic feel with a very laid back vibe. You can always go on a Wednesday or Sunday to catch a band playing. You can sit back and play some jenga while enjoying a nice pint of Dock Time or Little Cranky. They have 16 beers on tap ranging from seasonal IPA’s to New England style IPA’s. The outside matches the inside in feel and looks. In the warmer weather you can watch people play cornhole or bocce ball outside right on the water. At night you might find a fire outside to keep you and friends warm. The staff is friendly and the beers are cold. If you are looking for a nice spot to take your partner this might be it. You can find their beers in any many bars and package stores in Connecticut and New England.

Want to check out a different CT brewery for your date night? Check out this list of some of our other favorites!

2. Jonathan Edwards—North Stonington


This winery is tucked away in the pleasant town of North Stonington, home to about 5,000 residents. This small farm town gives this winery the perfect location to be an escape for any wine lover.

Jonathan Edwards has an elegant tasting room along with a tasting bar outside. Never had wine and don’t know what you like? The staff will help you find something that suits your taste and make sure you enjoy it all the way through. They are such a huge help to anyone who feels they are wine novice.

Any couple would enjoy walking through the grapevines outside or having an inside winery tour given by their trusted tour guide. They have an outside deck that gives couples a chance to sit out in the sun and look over the fields of grapes growing. People come from all around to this winery and has really earned its name of being one of the best. Making the drive is absolutely worth it, the combination of the knowledge of the staff and the overall beauty of the property is the reason people come far and wide to visit and experience truly great wine and atmosphere.

3. A Carriage Ride at Allegra Farm—Colchester

Allegra Farm

Do you want your date to believe they’re in a fairy tale? Looking an feeling a lot like the winter scene from Beauty and the Beast, Allegra Farm might be able to fulfill that dream for you. Taking part in one of Allegra farms magical carriage rides is something any couple can agree on.

Allegra Farm offers approximately a 1 hour ride for a variety of scenic routes. Make sure to place a reservation because they need to make sure everything is accounted for before you come. Carriage rides cost a $150 dollars if you pay cash, $175 for credit/check and weekend prices are $200 for cash and $225 for credit or check. You may be saying that this is a little expensive for a date night but something like this would make a great event for a special night.

Each carriage is an antique and resembles an early historical time period. These carriages and sleighs are so high quality that they have been used in the making of shows like Amistad, The Time Machine, Sex in the City, and Ed. If you want to experience a sleigh or carriage ride with your loved one right beside you, call and reserve a special night with Allegra Farm.

4. A Trip to the Casino

Great restaurants at Mohegan Sun

Are you someone who likes to wander? Fly by the seat of your pants? A trip to one of Connecticut’s casinos—Foxwoods or Mohegan Sun—could be the perfect date for a spur-of-the-moment, last-minute date night.

There’s almost always some sort of show or other entertainment happening in the various theatres or in the individual pubs, bars, and clubs, meaning that even if you went in the middle of the week, you’ll be able to treat your date to a live performance. After the show (or before—we don’t judge!) why not hit up the slots or tables and try your luck? There’s nothing like a little thrill to get the excitement pumping and make for a memorable date night.

And of course there are tons of options for dining. At Mohegan Sun, my personal favorite place to eat is the Hash House restaurant, which delivers truly huge portions for the hungriest of stomachs. (Check out this article for some other ideas about where to eat at Mohegan Sun!) When you get tired of all the eating, entertainment, and gambling, finish the night with a meander through the shops and spend some of your winnings.

5. Naskart—Montville, CT

Naskart_CT racing

Have a competitive spirit? Are you and your partner always trying to one up each other? Naskart is the place to be if this is you! Naskart offers memberships or just single day passes for driving and jumping. Yes, jumping. They have a trampoline park!

Hop into a go kart and take some hot laps. You can enjoy an amazing indoor track while competing against your partner or if you want, a group of friends. Naskart allows large groups to book group dates ahead of time and allows you to use their conference room for meeting up before big races, or switching gears and heading to the trampoline park. The trampoline park is located upstairs and overlooks the race track. If you want to be a spectator, you can jump upstairs as you watch your friends race around the track. If you need a place to cool down from all of the competition, you can head to the bar and grill to get some much needed refreshments. This is a great place to spend an afternoon and give into your competitive spirit. Head to their website to check out more about the drive and jump specials or set up a group event.

6. Taylor Brooke Winery —Woodstock


This beautiful Winery is located in WoodStock Connecticut tucked in the upper right corner of Windham county. They offer a space for guest to come and try wines and can sample up to two free wines and then pay for additional tastings. You can buy by the glass or by the bottle and these great wines can be enjoyed on the patio, pavilion or picnic tables overlooking the vineyard. This vineyard has its limited hours being the winter season and is open Saturday and Sunday from 11am-5pm. Tours are also available during the summer hours on Thursdays. They are by appointment only and it comes with a tour and tasting of ten wines. This event costs $30 per person and last about an hour. This tour takes you through the vineyard with a staff member as they teach you about history and journey of the vineyard. This winery is worth the distance to experience the breathtaking scenery and to enjoy a few glasses of exceptional wine. For any more information visit their website or give them a call.

7. Funny Bone—Manchester


This title speaks for itself, if you want to laugh and see some fun entertainment the funny bone in Hartford is here to help. The funny bone is the place to be for up in coming comedic talent. They offer food and drink for guest and the bar opens an hour and a half before the show starts so if you wanted to get there early to get the better seats and relax with a drink you can get first dibs on seating for the night. The food is upscale bar food for the crafty foodie in you. You can check out their line up schedule and much more from their website.

8. The Maritime Aquarium—Norwalk


Looking for a fun time in  Fairfield county? The Maritime Aquarium is a perfect destination for anyone of any age. They have two brand new exhibits. One is the sea turtle nursery, which is a place where you can follow a rescued baby loggerhead sea turtle through its first year of life and learn about how these turtles are born and how they care for this turtle. The other new exhibit is called the “Journey with the Jellies” which is where you can up close and personal with one of the most dangerous animals in the sea. These exhibits along with plenty of others provide anyone with the perfect date environment for you and your partner to explore and learn together in a fun environment.

9. Bridge Street Live—Collinsville


Bridge Street live is a venue that overlooks the Farmington River in the historical town of Collinsville. They feature live music, stand up comedy and other unique shows. They provide an elegant space for enjoying food and drinks while experiencing fun and entertaining shows. The view is amazing because of the location being so close to the Farmington River. Bridge Street Live is the perfect venue to bring a date because it allows you to unwind and be in a relaxed environment while still enjoying a great night of entertainment.

10.The Muse Paintbar—Glastonbury


This is the place to express your artistic abilities while enjoying a glass of your favorite type of wine or beer. You are lead by the trusted Muse paint instructors in painting whatever the chosen picture is for the night. You can enjoy a fun and free environment while trying to outdo your partner to see who can paint the best painting. This is an event where you can let loose and have fun with your partner and the group around you. The energy that is in the room the night of the painting is awesome. The happy and relaxed vibe is infectious and will take over even if you have a hard time replicating what the instructor is teaching.

11. Playwrights Hamden

If you enjoy a nice night out with some fine Irish dining, Playwrights in Hamden is the perfect spot for you. This fine establishment was actually where I had my very first Guinness. They have live music, trivia and food specials all the time. I used to visit for trivia night back when I was in college. My friends and I always loved seeing the same faces and just enjoying the fun and relaxing atmosphere. If you want to make sure you go on a night where something fun is happening, just check their Facebook for any updates.

12. Sunset Cruise — Essex

If you’re looking for an awesome evening on the water, the Essex Riverboat is waiting for you. For just $30 a person, you can enjoy the beautiful views of the Connecticut River. You hop aboard the Steam Train and take a quick 15 min ride to the dock. You get on the Riverboat for a 2-hour cruise down the river aboard the Becky Thatcher Riverboat. You can expect to be back at the station by 9:15. Enjoy some food and drinks as you take your journey out on the water. These fill up fast so plan on scheduling your trip a week in advance. You can make your reservations by following this link.

What do you think?

These are just some of the fun date night ideas that come to our minds when we think of unique things to do in CT. What about you? Do you have a favorite date night idea that you’d like to share with us? Let us know in the comments below and we might add it to the list!

About the author

Ryan Sylvestre

Leave a Comment

1 Comment