Unexpected Connecticut Last Updated: July 2022

Connecticut is full of surprises. Sure, we do quaint and beautiful like no other, but we’re much more than traditional. From unusual dining experiences and one-of-a-kind accommodations to adrenaline-pumping activities and more, here’s where to see a different side of Connecticut.


The Arts Scene

The arts are extra vibrant in Connecticut – and there are plenty of events and spots to celebrate them (many you may haven’t yet uncovered).

See awesome art installations like the touring Van Gogh immersive exhibit, the MLK Racial Equity Mural Tour, or the shimmering grotto inside the silo at Spring Hill Vineyards, also home to SHAG, a festival that connects artists with nature through creative collaborations.

But the arts in Connecticut aren’t just visual. You’ll find a wide range of film festivals and fantastic music venues throughout the state, showcasing every genre you can imagine.

Check out more arts festivals and destinations below.


Foodie Fun

It’s no secret that Connecticut has great restaurants (and even the nation’s #1 pizza) but the state’s foodie options aren’t all white tablecloths – we’ve got spots that put a unique spin on dining out.

Devour dishes at restaurants in repurposed spaces like Taquerio Mystic (a converted gas station) and The Station Restaurant (a former train station). Want to kick it up a notch? Try these unusual dining experiences from murder mystery dinners to immersive German dining and even brunch hosted by drag queens. Discover a plethora of unique plant-based eateries, then find photo-worthy bakeries, afternoon tea, and more with our Instagrammable Connecticut series.

Make all things brew when you check out not-so-typical breweries like 60’s-inspired Velvet Libations or Surfridge Brewing Company, offering a very west coast vibe. Want to drink without drinking? Sip flavors from the nationally acclaimed non-alcoholic brewing company, Athletic Brewing Co.

If you’re into picnicking, try turning up the dial with luxury picnics by The Picnic Gals or The Picnic Co – the whole setup will be provided, complete with décor, charcuterie, an irresistible aesthetic, and beyond.

Below are some more unique dining destinations.


Unique Outings & Destinations

When you spend the day (or weekend, or week!) in Connecticut, you don’t have to be ordinary – in fact, you can be anything but.

Get geared up with your group and ride New England’s first and foremost pedaled party and sightseeing bike, Elm City Party Bike. Drivers steer you through the streets cruising with the power of your legs and feet, and take you to popular bars, restaurants and shops offering guests drink specials. Or try a Taste of New Haven Tour to explore more of the city’s culinary culture.

For the daredevils, check off the “skydiving” line on your bucket list at Skydive Danielson, try rock or ice climbing with Ascent Climbing, or speed things up on a UTV tour with Backyard Adventure UTV Tours. And coming summer 2022, Club Getaway is opening one of the nation’s first bicycle ziplines: The Sky Cycle. Be sure to add it to your list!

If you're looking to get active indoors, let out your inner ninja at Thrillz Highflying Adventure Park, or try a variety of acrobatic-like activities from aerial yoga and pole dancing for fitness to troupe dance classes, chair dancing, equestrian vaulting, and more at Aerial Arts Fitness. Don't worry, you don't have to be a guru to have a good time — beginners are always welcome!

Here are some more out-of-the-box ideas.


Unconventional Accommodations

Come to Connecticut and get away the unique way. Stay in a helicopter, a treehouse, a storybook cottage, and beyond when you book a night at our most unconventional accommodations.

Here are some highlights to consider.