- Unique Date Ideas in Connecticut
- What to Do in Connecticut This Weekend
- The Most Fun Date Ideas in Connecticut
- 1. Explore Mystic
- 2. Hike to the Top of the World, Part 1: Heublein Tower
- 3. Catch a Flick at the Mansfield Drive-in Movie Theater
- 4. Dinner and a Show in Downtown Hartford and The Bushnell
- 5. Travel the Connecticut Wine Trail in Stonington
- 6. Look for Eagles with RiverQuest
- 7. Let Loose at Mohegan Sun Casino
- 8. Hike to the Top of the World, Part 2: Sleeping Giant
- 9. Main Street in Middletown
- 10. Take Them Out to the Ballgame with the Yard Goats
- 11. Get Awesome Pizza in New Haven
- 12. Paint, Wine, and Dine in Blue Back Square
- 13. Take a Scenic Road-trip Through Litchfield County
- 14. Hike to the Top, Part 3: Bear Mountain
- 15. Make a Tranquil Day of the Quiet Corner
- 16. Have a Few Cold Ones Along Rt. 1
- 17. Hang Out by the Water in Stonington Borough
- 18. Stroll Through Old Wethersfield
- 19. Catch a Sunset at Avery Point
- 20. Walk About the Cherry Blossoms in New Haven
- 21. Have Beer on the Lawn in Glastonbury
- 22. Take a Day Trip Out of the State
- Get Out There and Have Fun
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.
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.
If you’re visiting this post when it’s cold, be sure to see my list of great Connecticut winter activities. And because I love food, I’ll be sure to include some restaurant mentions for you with each of these recommendations!
What to Do in Connecticut This Weekend
The date ideas in this post will be useful all the time. But if you’re wondering what to do in Connecticut this weekend (or next), I also have advice for that. Check out these resources information on upcoming Connecticut events:
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, and Mango’s for wood-fired pizza .
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, too.
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 (see this post if you need a jeweler, BTW). 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.)
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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.
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 (see What to Do in CT This Weekend). 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.
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.
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), Krust (really good wood-fired pizza), and Tavern at the Armory (American fare).
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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 (like the Yale University campus) 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. It’s definitely one of the more fun things to do in Connecticut, especially given the walkable downtown area it’s located in.
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.
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). As one of Connecticut’s more relaxing date ideas, exploring Litchfield together can also be somewhat adventurous for sure.
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. Also consider seeing if Lion Rock Farm has any public events going on, if you’re interested in plants and such.
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!
Again, hiking is definitely one of the more fun things to do in Connecticut. Bear Mountain has plenty of beauty to prove it.
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.
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.
18. Stroll Through Old Wethersfield
If you enjoy walking through downtown city areas, but aren’t really city people, then Old Wethersfield is for you. It’s got restaurants, shops, ice cream, historic museums, and even a public river access area.
19. Catch a Sunset at Avery Point
Water views and sunsets go together like you and your partner. With that said, why not catch a sunset together at Avery Point in Groton? Home to Branford House and a UConn campus, this state-owned property offers a great westward vantage point. On any given evening, there’s plenty of parking.
Stop at Olio in Groton for dinner on your way out, or head over to Mystic or Stonington.
20. Walk About the Cherry Blossoms in New Haven
There’s a reason New Haven shows up on this list more than once. Every year around the last week of April, cherry blossom trees bloom in Connecticut. New Haven has a lot of these, especially in the Wooster Square area. There’s even a festival!
On your way out, stop over in nearby Derby for a couple of craft beers at The Hops Company (and maybe some Zuppardi’s Apizza, which is also served here).
21. Have Beer on the Lawn in Glastonbury
Tucked away in Glastonbury, way down a gravel road off the beaten path, is Hops on the Hill Farm Brewery. The beer here is pretty darn good (they also have plenty of non-alcoholic beverages to choose from, which is impressive). But the real beauty here is getting outside.
Hops on the Hill sits on a huge piece of property and they make a good portion of it available to visitors. Hungry? No problem: they host multiple food trucks at a time so you’ll have some options.
So load up the car with chairs or a blanket, get some snacks and sunscreen, and head here for an afternoon. You won’t regret it!
22. Take a Day Trip Out of the State
Yeah, maybe this one is cheating. But with Connecticut being so close to other great places, shouldn’t you take advantage? Consider taking a day trip to Boston, New York City, or Newport.
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!
I used the following references at different points in this post:
- “Six CT pizzerias make list of ‘best pizzas in America,'” Andrew DaRosa, New Haven Register
- “5 Reasons Why Couples Who Sweat Together, Stay Together,” Theresa E. DiDonato Ph.D., Psychology Today
- “Best 15 Things To Do in Connecticut’s Northeast (No-Longer-Quiet) Corner,” Malerie Yolen-Cohen, Huffington Post
- “Bear Mountain – Salisbury, CT,” BerkshireHiking.com
- “Bear Mountain (Connecticut),” Wikipedia
- “The Oldest Bar In Connecticut Has A Fascinating History,” Natalie Clunan, Only in Your State
- “The Griswold Inn,” Wikipedia
- “Dining Options at Mohegan Sun,” Mohegan Sun Casino
- “Sleeping Giant Tower,” CTMQ
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