The 203 Summer Bucket List - Part 1

Sum·mer Buck·et List: Unique and unforgettable experiences to tackle right here in Connecticut this summer.

Every summer has a story- and we’re here to help make yours legendary. To help you make the most of Summer 2025, we’re kicking off our Summer Bucket List Series with a curated list of must-do adventures across the state. From floating cocktail boats to waterfall hikes and golden hour sails, these experiences are what summer dreams are made of.

We’ll be rolling out more bucket list ideas all season long, and we want to hear from you- what should we include in Part 2?

As you start checking things off, don’t forget to tag us in your adventures using #203SummerStory for a chance to win a free 203 Baseball Cap. We’ll be picking 2 winners in July and 2 in August… so get out there and make it count.

Farmington River Tubing - Farmington, CT

If you haven’t floated down the Farmington River yet… this is your sign. This iconic summer adventure kicks off at Satan’s Kingdom State Rec Area (yes, that’s really the name) and sends you on a few miles of pure river bliss- complete with rapids, rocks to lounge on, and unbeatable summer scenery.

Your rental includes everything you need for a laid-back day on the water: a durable tube, a life vest, and a bus ride back once you’ve floated your way downstream. We recommend packing a dry bag with lunch and pulling over on one of the big river rocks for a mid-float picnic (this is our fave part!). 

Pro tip: Skip the crowds and go midweek for zero lines and max chill. And call ahead or check their site for daily hours and river conditions before you head out!

Brownstone Adventure Park - Portland, CT

If you're looking to level up your summer, this is the move. Brownstone is an old quarry turned full-blown outdoor adventure park- with zip lines, cliff jumps, rope swings, floating obstacle courses, and giant waterslides. It's like your favorite summer camp... but way more intense (in the best way). Whether you're there for the adrenaline or just want to float and watch your friends go full send, it’s an epic way to spend a hot summer day.

Powder Ridge Waterslide - Middlefield, CT

Yes, Powder Ridge is a ski mountain - but in the summer, it turns into an absolute waterpark dream. Their giant inflatable water slide shoots you down the slope at full speed, and trust us, it’s just as wild as it sounds. It’s the kind of adrenaline rush that’ll have you laughing the whole way down (and going back for round two). Fast, fun, and totally unexpected - this is a summer bucket list win.

Take a Cruise on the Thimble Islands - Branford, CT

Just off the coast of Branford, you’ll find one of Connecticut’s best-kept secrets: the Thimble Islands. This cluster of tiny, privately-owned islands feels like something out of a storybook—think pink granite shores, whimsical cottages, and sailboats drifting by like it’s no big deal.

While most of the islands are private, there are a couple of boat tours that give you an up-close look at this magical little slice of the Connecticut coast- and spill all the fun facts, legends, and local lore along the way.

We highly suggest hopping on a narrated cruise to explore them by boat and soak up stories of pirates, private islands, and old New England legends.

Two Cruises that we recommend: The Seamist & The Islander

The Seamist offers a breezy ride with two decks and a bar onboard (yes, you can sip while you sail), while The Islander - a small, local-led tour known as “The Little Boat” - brings you up close with island life and insider stories. Either way, this one’s pure summer magic.

Pearl the Oyster Boat - Rowayton, CT

Tucked behind Rowayton Seafood, this beautifully restored cocktail boat is one of the dreamiest spots to sip and unwind in coastal CT. Think craft cocktails, freshly shucked oysters, good company, and golden-hour views of the Five Mile River - all without ever leaving the dock. With only 30 guests allowed aboard at a time, the vibe is intimate, elevated, and effortlessly chic. It’s 21+ only, and yes, you’ll need a reservation… trust us, you’ll want one.

Sushi Making Class - Statewide 

If you’re looking for a summer hang that’s equal parts fun and memorable, The Sushi Class delivers. They’ll come to you with everything you need for a private sushi-making party - perfect for birthdays, girls' nights, or just a unique excuse to gather your crew. You can also catch one of their ticketed pop-up classes at cool spots around the state (check their website for upcoming dates). It’s hands-on, low-pressure, and way more fun than dinner and a movie.

Sunset Cruises & Sunset Paddles

Norwalk Seaport Association - Norwalk Islands Sunset Cruise

Hop aboard the Norwalk Seaport Association’s 45-foot catamaran for one of the dreamiest ways to end a summer day. This two-hour cruise glides through Norwalk Harbor and out toward the islands, giving you front-row seats to some seriously stunning sunset views over the Sound. It’s peaceful, scenic, and the perfect excuse to slow down, sip something cold, and take in golden hour from the water.

SoundWaters Sunset Sail - Stamford, CT

Hop aboard their 80-foot schooner for a dreamy sunset sail through Long Island Sound - BYO snacks and drinks encouraged. It’s low-key, breezy, and the perfect way to soak up golden hour by the water. Feeling adventurous? They also offer kayak and paddleboard rentals during the day.

Sea Kayak CT - Westport, CT

There’s something magical about paddling the Saugatuck River at sunset - and Sea Kayak CT delivers. From guided sunset and full moon tours to firework paddles and daytime rentals, they’ve got options for every vibe. It’s the perfect mix of adventure and laid-back coastal energy.

Goat Yoga at Nadeau Farm - Hamden, CT

If you've never done downward dog with a goat on your back… you’re missing out. Nadeau Farm’s goat yoga classes are the perfect mix of calming and completely chaotic - in the best way. You’ll stretch, breathe, and try to keep it together while baby goats bounce around doing their own thing. It’s wholesome, hilarious, and basically guaranteed to boost your mood.

Indian Well State Park - Shelton, CT
Tucked along the Housatonic River, Indian Well is the kind of summer spot you’ll want to keep going back to. A short, shady hike leads you straight to a gorgeous waterfall. It’s peaceful, refreshing, and feels like a little slice of New England magic. Pack a picnic, bring your friends, and make a day of it. This one’s a must for any CT summer bucket list.

Free Outdoor Music: 

Levitt Pavilion - Westport, CT

Levitt Pavilion brings over 50 free outdoor shows to downtown Westport every summer, from local favorites to national acts. Most shows are free, but you’ll want to reserve tickets online or swing by the box office a couple hours before showtime. Set up by the river, bring your picnic, and enjoy the music under the stars.

Bayley Beach & Pinkney Park - Rowayton, CT

Spend your Sunday nights the Rowayton way - with live music by the water and unbeatable summer vibes. Free concerts kick off in June, starting at Bayley Beach and moving to Pinkney Park later in the season. Music starts at 5:30 PM, so pack a picnic, grab your crew, and settle in for the perfect end to your weekend.

Sherman Green Gazebo - Fairfield, CT

Nothing says summer like live music on the green. On Thursday and Sunday evenings from May through August, head to the Sherman Green Gazebo for free, family-friendly concerts with everything from acoustic sets to local bands. Bring a blanket and let the good vibes roll. (May we suggest reserving an outdoor table at Centro and enjoying the music from their patio?) 

Live Music: Ticketed

Hartford Healthcare Amphitheater - Bridgeport, CT

This open-air venue in the heart of Bridgeport is not your average concert spot. With a killer lineup of national acts, stadium-style energy, and a breezy coastal vibe, it’s one of the best places in the state to catch live music all summer long. The sound is top-tier, the seats are close to the action, and there isn’t a bad view in the house. Whether you're rocking out with friends or just there for the vibe, this place always delivers.

Xfinity Theatre - Hartford, CT

Xfinity Theatre in Hartford is Connecticut’s go-to spot for big outdoor concerts. With plenty of lawn seating and great vibes, it’s perfect for catching all your top artists in the summer. Whether it’s rock, pop, or country, the music’s always live and the energy’s always high.