Connecticut’s got a ton going on as May winds down. Whether you’re into coastal views, quirky towns, or a little bit of culture, there’s no shortage of ways to fill your week. Seriously, you’ll find both indoor and outdoor adventures that show off just how varied and interesting this state can be.
The weather’s finally cooperating, which means it’s prime time to wander through Connecticut’s parks, small towns, and city neighborhoods. Memorial Day celebrations are still echoing in a few spots, and plenty of museums and theaters are rolling out special programs for the season. Here are some picks—some local favorites, some you might not have tried yet.
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1) Attend the Connecticut Strawberry Festival at Priam Vineyards, Colchester, June 7-8
The festivals.com/connecticut-strawberry-festival-101640″>Connecticut Strawberry Festival comes back to Priam Vineyards in Colchester on June 7-8, 2025. It’s free to get in and everyone’s welcome, from kids to grandparents.
Picture 80+ vendors scattered across the vineyard at 11 Shailor Hill Road. Saturday runs 11am-7pm, and Sunday’s about the same.
Food stands are loaded with strawberry treats—some classic, some a little wild. Adults can sample wine, including the vineyard’s own strawberry-infused bottles.
Bring a blanket and sprawl out on the lawn for live music both days. Local bands set the vibe while you check out crafts and fresh produce.
Parking gets tight fast, so showing up early is your best bet. Carpooling’s not a bad idea, and you’ll want decent shoes since the festival covers a lot of ground.
2) Explore Tyler Mill Preserve hiking trails in Wallingford
Tyler Mill Preserve sprawls across about 1,000 acres in Wallingford, offering a mix of woods, fields, and streams. Hikers of all skill levels can find a trail that fits.
If you’re up for it, the 7.7-mile loop is a moderate challenge, usually taking around 3 hours. Prefer something shorter? The Orange and North Red Trail Loop is just 1.6 miles and takes about 40 minutes—good for families or anyone not looking to overdo it.
You’ll walk past streams, through woods, and across open fields. The landscape changes as you go, so it doesn’t get boring.
Wear sturdy shoes since some paths get a little rough. There’s a lot of variety and challenge out there, so just pick a trail that fits your mood and energy.
3) Visit the Peabody Museum of Natural History in New Haven
The Yale Peabody Museum is a solid pick for a day out. After its recent makeover, it’s packed with dinosaurs, minerals, and artifacts that bring the planet’s story to life.
It’s right on Yale’s campus, with free parking close by. Look for the painted dinosaur tracks on the sidewalk—they’ll lead you right in.
No need to worry about tickets or timing for regular visits anymore, so you can just drop by when it suits you.
The dinosaur exhibits are a highlight, and honestly, adults seem just as into them as kids. Their fossil collection is one of the best in the region.
There’s more than just dinos, though. You’ll find cool geology, anthropology, and natural history displays. And if you’re the type who likes to dig deeper, check their calendar for public lectures or workshops.
Give yourself a couple of hours to really see everything. The Peabody Museum pops up on just about every “best of New Haven” list, so it’s worth squeezing in this week.
4) Experience live music events in Connecticut venues this weekend
Connecticut’s music scene is buzzing this weekend. The Loveland Hill Band is playing at one of several outdoor festivals, and you’ll find all sorts of acts across the state.
There’s everything from acoustic shows to full orchestras. Many Memorial Day events still have music as part of the fun.
Outdoor concerts are popping up everywhere—parks, bandshells, you name it. Bring a blanket, maybe a picnic, and settle in under the May sky.
If you’d rather be inside, theaters and music venues are rolling out special holiday weekend lineups too.
Styles run the gamut: classical, indie, rock… no shortage of options. Some places even pair live music with food trucks and games for a full evening out.
5) Enjoy boat excursions and cruises on Connecticut’s rivers and coastline
Connecticut’s rivers and coastline are perfect for exploring by boat this time of year. The weather’s right, and the views? Even better from the water.
Hop on the Essex Steam Train & Riverboat for a combo rail-and-river ride through the Connecticut River Valley—definitely a different perspective than you’d get by car.
If you want something more laid-back, Argia Mystic Cruises offer sailboat trips around Mystic Harbor. Their smaller boats can sneak into scenic spots the bigger ones miss.
Smaller groups might like a one-hour fun boat ride on the Connecticut River—up to six people, so it’s ideal for families or friends.
The Thimble Island Cruise is a local classic. You’ll wind through a cluster of small islands and hear their quirky histories.
Most sightseeing cruises run rain or shine. Book ahead—weekend spots disappear fast when summer unofficially kicks off.
6) Attend outdoor festivals marking the summer kickoff across Connecticut
Festival season is going strong. Even though Memorial Day’s passed, Connecticut’s still hosting a bunch of outdoor events to ring in summer.
Festivals are everywhere—music, food, crafts, you name it. Some towns just keep the party going right through the end of May.
Family-friendly carnivals with rides and games usually run Thursday to Sunday, and hours stretch out as the weekend nears.
Music fans will find outdoor concerts on town greens and in local parks. Bring a picnic, pick a spot, and enjoy everything from orchestras to cover bands in the mild weather.
Farmers markets are getting bigger, too, with more local produce and extras like crafts or food trucks.
Coastal towns like Mystic and Essex put on maritime-themed festivals—think seafood, boat displays, and water sports. It’s a great way to dive into Connecticut’s summer shoreline scene.
7) Try your luck at Foxwoods Resort Casino
Foxwoods Resort Casino isn’t just about gambling (though there’s plenty of that, if you’re into it). In Mashantucket, this place is huge—slots, poker, blackjack, roulette, all the classics.
You’ll also find great dining and shopping. Entertainment events change weekly, so you never quite know what you’ll stumble on.
Need a breather from the casino? The Pequot Hiking Trails are right nearby, offering a quick escape into the woods.
For a bit of an adrenaline rush, the HighFlyer Zipline gives you a wild aerial view over the property.
Lately, trivia nights have been drawing crowds—worth asking about if you want a different kind of night out.
It’s open 24/7, so you can swing by whenever the mood strikes.
8) Explore Hammonasset Beach State Park and Meig’s Point in Madison
Hammonasset Beach State Park is Connecticut’s biggest shoreline park, with over two miles of beach—perfect for a late-May trip before the summer rush.
Walk, bike, or kayak through beaches, wetlands, and woods. The trail system is pretty user-friendly, no matter your ability.
Don’t miss the Meigs Point Nature Center. This free spot has 4,000 square feet of interactive exhibits for all ages.
Wildlife is everywhere right now, so bring binoculars if you’re into birdwatching. Migratory birds are making their return.
Swimming areas might not have lifeguards yet, so be careful if you go in—the water’s still chilly, too.
Weekdays are quieter, but even then, this place can get busy on sunny days. Parking’s decent but fills up fast on weekends.
9) Visit Waterford Beach Park for outdoor relaxation
Waterford Beach Park is a low-key spot for anyone craving a peaceful day by the water. Right on Long Island Sound, the beach is clean and the water’s usually calm—great for swimming or just chilling out.
You’ve got the basics covered: lifeguards, clean bathrooms, and outdoor showers for rinsing off before you leave.
There’s more than just sand, though. Ball fields invite pickup games, and the covered pavilions with BBQ grills make it easy to throw together a picnic.
Want to see what’s happening? Check Eventbrite for upcoming events—things like “Junk in the Trunk” sales or sound meditation concerts pop up now and then.
Arrive early on weekends if you can; parking doesn’t last long. The fee’s seasonal and not too steep compared to other state beaches.
10) Experience car races happening locally this weekend
If you love car racing, Connecticut’s got some options this weekend. The Sport Hill Races in Easton are putting on a Hill Climb Demonstration alongside an Antique Car Show this Saturday, May 24, at the Easton Town Library Parking Lot. It runs from 10:00 am to 2:30 pm, and anyone can drop by to check out historic racing and classic rides.
Thompson Speedway has stuff going on this month too, but you’ll want to peek at their current schedule to see what’s actually happening this weekend. Thompson’s been around for ages and still feels like the real deal if you’re after that classic speedway vibe.
If you’d rather get in on the action instead of just watching, Connecticut actually has driving courses where you can hop behind the wheel. It’s a safe way to get a taste of speed, with pros showing you the ropes.
Missed the Cars 4 Paws Car Show earlier this month? No worries—these kinds of events pop up all the time in Connecticut, especially when the weather gets nice. They’re a fun mix of car love and community energy.
If you’re heading to a race, showing up early is smart if you want a good spot. I’d bring sunscreen, water, and maybe earplugs—some of those engines are seriously loud.
Tips for Making the Most of Your Connecticut Visit
Connecticut’s small enough to explore a lot in a short time, but you’ll want a bit of a plan. The landscape and weather can flip on you, so being ready for anything helps.
Weather and What to Pack
May in Connecticut can’t really make up its mind. You’ll usually get daytime temps between 60-75°F, but nights can drop to the mid-40s or 50s. Bring layers you can peel off or pile on as needed.
Spring showers are pretty common, so toss a lightweight rain jacket or umbrella in your bag. You’ll want comfortable shoes if you’re hitting up hiking trails or state parks.
If you’re headed toward the coast—say, Hammonasset Beach—don’t skip the sunscreen. Even cloudy days can sneak up on you with the UV, especially near water.
Museums like the Yale Art Gallery keep things cool inside, so a light sweater isn’t a bad idea.
Transportation Options Across the State
Getting around Connecticut isn’t too tricky, but it’s easier if you sort out your transportation ahead of time. Renting a car gives you the most freedom, especially if you want to check out places like Gillette Castle State Park or anywhere rural.
Public transit covers the basics. Metro-North runs from NYC up through the coast, and CTtransit buses hit the bigger cities. Amtrak’s Northeast Corridor line stops at places like New Haven, Hartford, and Mystic.
Rideshares are easy to grab in cities, but in rural spots they can be spotty—sometimes you’ll want to book ahead if you’re heading out there.
Weekend Travel Tip: Memorial Day Weekend traffic can be brutal, especially on I-95 and I-91. If you can, travel before 2pm or after 7pm to dodge the worst of it. Nobody likes sitting in a jam when there’s stuff to do.
Connecticut Event Planning Resources
Planning a trip here? You’ll want some solid info to make the most of it. Here’s where I’d start.
Where to Find Official Event Calendars
CTvisit has a pretty thorough weekend events page that’s always being updated. You’ll find festivals, art shows, outdoor stuff—whatever’s happening statewide.
Local tourism boards get more specific for their areas, and the Connecticut Visitor Guide posts weekly roundups with planning tips.
For arts and music, CT Insider’s monthly calendar is worth a look—concerts, theater, exhibits, you name it.
And don’t forget about Facebook Events or Eventbrite. You can search by date, town, or even niche interests, and a lot of venues put their latest schedules and ticket info right on their own websites.
Safety and Accessibility Considerations
Before heading out to any outdoor event, check the weather and dress for it. Connecticut in late May is unpredictable—maybe it’s warm, maybe you’re wishing you’d brought a jacket. Layer up, just in case.
Most big attractions post accessibility details online, but honestly, it’s worth calling ahead if you’ve got specific mobility needs or questions. Sometimes the info online is just… not enough.
If you’re looking for family-friendly spots, Chelsea Piers in Stamford and Golf Quest Family Sports Center are solid picks. Both have controlled environments, so you’re not worrying about the little ones running wild.
Public transportation is a mixed bag. You’ll find decent bus coverage around Hartford, New Haven, and Stamford, but once you’re out in the sticks, good luck. In those cases, ride-sharing apps might be your best bet.
Parking can get tricky, especially during Memorial Day weekend events. Crowds show up early, and lots fill fast. Always check the event’s website for parking info and possible fees—nobody likes surprise charges.
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