Connecticut proposal photo of a newly engaged couple.

Unique Date Ideas in Connecticut

We’ve all been there: you’re with a great person and are thinking of special things to do with them. You want to have fun and make the time together memorable. And while I’m definitely not an expert on the dating scene in our state, I do have some suggestions for fun, romantic, and unique date ideas in Connecticut.

In my humble opinion, every single one of the ideas on this list of date ideas applies whether you’re dating, planning your wedding, or already married. Many of them are kid-friendly, so they could even apply to family outings in our state.

Connecticut proposal photo of a newly engaged couple.

With the state being so small, are there actually any fun Connecticut date ideas?

Perhaps surprisingly, the answer is a certain “yes.” While Connecticut may be a small state, we have a lot of diverse aspects that result in plenty of cool things to do on a date. There’s water (both ocean and rivers), mountains (if you want to call them that), and an awesome mix of towns and cities filled with great restaurants and more.

And because I love food, I’ll be sure to include some restaurant mentions for you with each of these recommendations!

17 of the Most Fun Date Ideas in Connecticut

1. Explore Mystic

Mystic just about has it all, which is why it should be the first Connecticut date idea that you consider. There’s an aquarium, a historic shopping center, two rivers with boating options, art, and tons of food and drink options. 

One great thing about Mystic as a date idea is that depending on the time of year, you can go there day or night. This makes Mystic awesome for day dates and night dates alike. And the food and drink options are too plentiful to list. Some of my favorites are Red 36 for seafood, Oyster Club for eclectic fare, Mango’s for wood-fired pizza, and Latitude 41 for river-side ambiance. 

If you’re looking for a romantic Mystic date idea, I’d definitely factor in something on the water such as a ride on the Argia. And by the way, Mystic has some great wedding venues.

2. Hike to the Top of the World, Part 1: Heublein Tower

Active couples, look no further than a hike up to Heublein Tower at Talcott Mountain State Park in Simsbury. I already pointed out that this is a great place to propose. Naturally, then, it’s a great option as an active date idea at only 1.25 miles in length from bottom to top. Check out the trail map then point your GPS to for parking.

Hiking in general is a strong category of fun date ideas in Connecticut. We don’t have “true” mountains here, so most outings are moderate and easier. And it’s like they say: couples who sweat together stay together.

Once you two catch your breath, take a short drive down to Andy’s Italian Kitchen, La Joya, or Millwright’s for a rewarding meal. (By the way, I think Heublein Tower is a great place to propose, once you get to that point.)

3. Catch a Flick at the Mansfield Drive-in Movie Theater

This has to be one of the most unique date ideas in Connecticut. The Mansfield Drive-in is an old-school drive-in movie theater near UConn’s Storrs campus. It opens for business every spring and even has a snack bar. Perhaps best of all, every ticket actually gets you access to a double feature of two movies.

Bucking the trend a little bit, I’m going to suggest that you just eat here at the drive-in’s snack bar. Because who doesn’t like movie theater food? And don’t forget to drop by the UConn Dairy Bar for some ice cream on your way home.

4. Dinner and a Show in Downtown Hartford and The Bushnell

If the performance arts are your thing and/or you’re looking for a cinematic date idea for a special occasion, consider watching a show at The Bushnell. Located in downtown Hartford, it offers everything from Blue Man Group performances to jazz concerts to Broadway shows. 

Several modern dining options are within close Uber distance. Salute and Republic at The Linden are both solid options offering reservations. Or if you’re feeling a little more casual and adventurous, give Bear’s Smokehouse a try.

5. Travel the Connecticut Wine Trail in Stonington

Making for a great spring or summertime Connecticut day date plan, exploring our state’s wine trail in Stonington is a superb thought. Saltwater Farm Vineyard, Stonington Vineyards, and Jonathan Edwards are your three prime choices.

As far as food goes, consider doing it picnic style by stopping at one of the two Mystic Market locations in the area.

6. Look for Eagles with RiverQuest

Here’s another unique Connecticut date idea for you: go bird/nature watching on the water with RiverQuest. Associated with the Connecticut River Museum in Essex (but sometimes departing from Haddam, based on my experience), this company offers themed public and private cruises. Trips run throughout most of the year and you can bring your own wine on board. If you plan this one well, it’ll be one of the more romantic date ideas in Connecticut for sure.

Right down the street from the museum is The Griswold Inn, the oldest bar in Connecticut and one of the oldest in the country. They have some good drinks and sandwiches.

7. Let Loose at Mohegan Sun Casino

If you’re looking for a glamorous date night idea, Mohegan Sun Casino may be for you. Located in Uncasville, this place is sort of a world of its own. You can place bets. There are live shows and sports. You can take part in whiskey tastings. There’s even a spa and a hotel. You could even golf or just go shopping. The casino is so versatile has huge potential for being one of the most unique date ideas in Connecticut.

One of the best reasons to go to Mohegan Sun is to eat. There are 45 establishments to choose from, including the aforementioned Frank Pepe Pizzeria Napoletana.

8. Hike to the Top of the World, Part 2: Sleeping Giant

Not too far from New Haven is Hamden, the home of Mount Carmel in Sleeping Giant State Park. Hiking couples might love this Connecticut date idea since there are some 30 miles of trails to enjoy. If you’re looking for views, then the 1.6-mile Tower Trail is for you. 

When you’re done, reward each other with ice cream from Wentworth Homemade Ice Cream or take a drive over to New Haven for some pizza.

9. Main Street in Middletown

If Greater Hartford nightlife with wining and dining is your thing, then a date on Main Street in Middletown might be a good idea. Parking and walking or Ubering might be a safe bet as you enjoy popular spots such as La Boca (Mexican), Mondo (Italian), and Krust (really good wood-fired pizza). 
Venture out a little bit and grab some great beer at Stubborn Beauty or Concentric Brewing (technically Portland) while you’re at it.

10. Take Them Out to the Ballgame with the Yard Goats

Even if baseball isn’t your thing, consider catching a Yard Goats game at Dunkin’ Donuts Park in Hartford during the spring or summer. I must admit that it’s actually a pretty good date (or double date) idea. You get to enjoy some fresh air, beer, and summer food. If you’re baseball fans to begin with, then that makes this Connecticut date idea all the better.

After the game, do yourselves a favor and walk over to City Steam Brewery while you leave your car in the lot.

11. Get Awesome Pizza in New Haven

Arguably, Connecticut has the best pizza in the country (OK, New York pizza probably wins, but I haven’t had enough of it to argue). Understandably, I have to give a nod to New Haven and its wonderful pizza options as a fun date idea in Connecticut. 

Frank Pepe is probably at the top of this category (yes, they have locations elsewhere such as Manchester and in Mohegan Sun Casino). Zuppardi’s and BAR are delicious, too. Several of the popular pizza places are in the Wooster Square area of the city, which could make for a really fun date idea in Connecticut if you like walking around. Speaking of which…

It’s not just about the pizza! Another thing that makes New Haven a great Connecticut date idea is that much of this city is beautiful and quite walkable. There are plenty of architectural sights to behold and established parks to chill out in. Grab a tour with Walk New Haven and see for yourself!

12. Paint, Wine, and Dine in Blue Back Square

Here’s a really unique Connecticut date idea: go painting together at Muse Paintbar in West Hartford’s Blue Back Square. The basic premise is that you check their calendar, choose a date and painting that you like, then reserve your spots all online.

While this is somewhat of a unique date idea in Connecticut, I’d say that it can be equally a romantic date idea. When you show up, you can grab some snacks and drinks at the bar and enjoy those as your artist leads you through the painting process. Part of the reason Muse makes for a great date is that you bring your paintings home afterwards!

One of the best things about this particular Muse location is that Blue Back Square itself is a great spot for walking and dining. After you paint, consider taking a stroll to Fleming’s, Restaurant Bricco, or Barcelona for a bite.

A man and woman who just got engaged pose inside of a Muse paint studio.

13. Take a Scenic Road-trip Through Litchfield County

The northwestern corner of Connecticut, Litchfield County, could be made into a single date idea or multiple. In my experience, the overall vibe is pretty laid back in this area. Couples who like the outdoors will appreciate its beauty and drivability. Attractions include the West Cornwall Covered Bridge, Topsmead State Forest, Litchfield Distillery, and Haight-Brown Winery (the oldest in the state). Litchfield County is especially gorgeous in the fall (peak foliage is in early October).

If you’re looking for something to eat while planning this fun date idea in Connecticut, consider The Village Restaurant, Toast & Co. (breakfast and lunch only), or Community Table.

Taking a roadtrip is a great Connecticut date idea.

14. Hike to the Top, Part 3: Bear Mountain

For serious hikers, Bear Mountain in Salisbury is the tallest summit in our state. Located way up in Litchfield County, this is definitely an active Connecticut date idea. The views are apparently well worth the six-mile round trip!

Since you’ll be in the area, I’d recommend stopping for a meal at Blackberry River Bistro in Canaan after. 

15. Make a Tranquil Day of the Quiet Corner

Like the northwest part of the date, the Quiet Corner in the northeast makes for an excellent Connecticut road-trip date idea. This Windham County idea is ideal for a laid-back day date for sure. There are several places to check out up here, from a tour of Roseland Cottage to a stroll through downtown Putnam. A fall drive would make for an especially romantic date idea; peak foliage hits this part of the state in early October. 

If you like pub food, be sure to check out Black Dog Bar and Grille in Putnam while you’re up there.

16. Have a Few Cold Ones Along Rt. 1

In addition to wine, breweries and taprooms make for really good Connecticut date ideas. The Route 1 corridor in the southwestern part of the state is particularly popular for this. Here, you’ll find Two Roads Brewing in Stratford (maybe our state’s most widely known beer-maker), Fairfield Craft Ales in Stratford (also known for live comedy and music), and Tribus Beer Co. in Milford.

Popular food in the area includes Lasse’s Restaurant for Italian, Mac n’Out for creative macaroni and cheese, and Bridge House Restaurant.

A couple on a date hold hands in Stonington Borough, Connecticut.

17. Hang Out by the Water in Stonington Borough

Stonington Borough is an awesome alternative to the usual romantic Mystic date idea. Located about 10 minutes away but also in southeastern Connecticut, this is a quaint town with a cool downtown vibe area situated on a one-way street which runs along Stonington Harbor (aptly named Water Street). 

But that’s not all, as The Velvet Mill offers some really cool shopping and art options for you to check out. That’s also where Beer’d Brewing Co. is, which has some of the best New England-style beers you’ve ever had.

Perhaps best of all, at the end of Water Street you’ll find Stonington Point, The Stonington Lighthouse Museum, and Dubois Beach. These are public areas perfect for a stroll any time of year.

There’s no shortage of good food in this small area. Dog Watch Cafe, Milagro Cafe, and Breakwater are awesome bets.

Get Out There and Have Fun

So yeah, Connecticut is small. Undoubtedly, you’re now ready to conquer the dating scene after reading this post. Get out there and have some fun. If you have some other suggestions for this list, please drop a comment below or send me an email!

Citations

I used the following references at different points in this post:

  1. “Six CT pizzerias make list of ‘best pizzas in America,'” Andrew DaRosa, New Haven Register
  2. “5 Reasons Why Couples Who Sweat Together, Stay Together,” Theresa E. DiDonato Ph.D., Psychology Today
  3. “Best 15 Things To Do in Connecticut’s Northeast (No-Longer-Quiet) Corner,” Malerie Yolen-Cohen, Huffington Post
  4. “Bear Mountain – Salisbury, CT,” BerkshireHiking.com
  5. “Bear Mountain (Connecticut),” Wikipedia
  6. “The Oldest Bar In Connecticut Has A Fascinating History,” Natalie Clunan, Only in Your State
  7. “The Griswold Inn,” Wikipedia
  8. “Dining Options at Mohegan Sun,” Mohegan Sun Casino
  9. “Sleeping Giant Tower,” CTMQ

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