Spring’s finally settled into Connecticut, and it’s about time. Warm days are here—perfect for getting out and exploring. The third week of May brings a fun mix of cultural events, outdoor adventures, and food festivals across the state. Honestly, you don’t need to overthink your plans this week; Connecticut’s packed with easy, accessible activities for just about anyone.
The state’s mix of coastline, rolling hills, and historic towns really shines in May. Whether you’re after a laid-back getaway or something with a bit more energy, you’ll find options that show off Connecticut’s heritage and natural beauty. The weather usually cooperates, so indoor and outdoor plans are both fair game.
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1) Connecticut Barber Expo, May 17-19, 2025
The Connecticut Barber Expo lands at Mohegan Sun Casino in Uncasville this weekend. It’s billed as the world’s largest men’s grooming event—think trade shows, live demos, and some wild hair competitions, all under one roof.
The festivities kick off with the Barber Grammys on Saturday night (8:30 PM to 1:00 AM). This gala celebrates top barbers and has become a real highlight.
Over three days, you’ll catch master barbers showing off their skills, shop for pro tools, and catch up on the latest grooming trends. Celebrities and influencers tend to make an appearance, adding to the buzz.
If you’re an aspiring barber, don’t miss the educational sessions—industry veterans share tips that might just level up your game. There’s plenty of networking and maybe even a few tricks to bring home.
Tickets are available for single days or the whole weekend. It’s a popular event, so grabbing tickets early is smart if you want in.
2) Food Truck Battles Festival, Saturday, May 17, 2025
The CT Food Truck Battles Festival rolls back into Wolcott this Saturday at Woodtick Recreation Area. It’s a gathering of Connecticut’s best food trucks, all competing for your vote.
You’ll get to try a wild variety of eats as vendors go head-to-head. And it’s not just food—live music and entertainment keep things lively all day.
For those who like a challenge, there are eating competitions that add a little extra spice. Beer gardens are scattered around for when you need a cold drink with your meal.
The festival actually runs all weekend (May 16-18), but Saturday’s the big day with the main events and the biggest crowds. Show up early if you want to sample the most trucks before lines get long.
Tickets are on sale now, and they tend to go fast. There are rides and vendor booths, too, so it’s a solid pick for families.
3) Goat Days Festival in New Milford
New Milford GOAT Days is back at Young’s Field from May 16-18. If you’ve got time on Sunday, you can still catch this spring favorite that’s part farm event, part carnival.
The big draw? Baby goat hugging. Yep, you can actually snuggle baby goats—kids and adults both seem to love it.
There’s more to do: pet bunnies, take a pony ride, or just soak up the carnival vibe.
Carnival rides and food trucks are scattered around, and local vendors offer snacks and handmade stuff.
If you’re feeling adventurous, hot air balloon rides give you a fresh view of New Milford—weather permitting, of course.
By showing up, you’re supporting local businesses and nonprofits. Parking’s on-site, but if you want a close spot, get there early.
4) Visit Foxwoods Resort Casino
Foxwoods Resort Casino in Mashantucket isn’t just about gaming. It’s a full-on entertainment complex with something for everyone.
Check out live shows, concerts, and performances—big names show up pretty regularly, so peek at the schedule before you go.
If you need a breather, the Pequot Hiking Trails let you stretch your legs and see some of Connecticut’s natural side.
Dining options range from quick bites to fine dining. Shopping? Plenty of that, too.
Bringing the family? Foxwoods has activities for all ages. The Monza World Class Karting track is a hit with adrenaline seekers.
You’ll also find spas, museums, and tons of other things to do. Even if you’re not into gambling, you won’t get bored.
5) Explore Mohegan Sun Casino
If you’re after some excitement, Mohegan Sun in Uncasville has you covered—gaming, dining, and live events all in one spot. Try your luck at a huge selection of casino games.
But it’s not just about gambling. The concerts and shows this week are worth a look, with big acts often playing the Mohegan Sun Arena.
Need a break? Grab a bite—choices range from quick eats to high-end spots. The Vista Lounge at Wombi Rock is a favorite for drinks and people-watching.
If you’re in the mood to unwind, the Elemis Spa is a solid pick for some R&R. And if shopping’s your thing, the resort’s got you covered.
Mohegan Sun’s easy to find, and parking’s rarely an issue.
6) Hiking at Waterford Beach Park
Waterford Beach Park isn’t just for swimmers. Several scenic hiking trails wind through the coastal woods, offering a chill alternative to just hanging on the sand.
The main trail starts near the parking lot and runs about a mile along the shore. You’ll catch some sweet views of Long Island Sound, and the path’s flat enough for most folks.
Heads up: it’s a bit of a walk from the parking lot to the trails. The trek from parking to the beach is decent but nothing too crazy.
Bring water and wear comfy shoes—terrain shifts from packed dirt to sandy patches. Trails are usually in good shape, though they can get muddy after rain.
Early mornings are best if you want peace and cooler temps. Keep your eyes peeled for shore birds and, if you’re lucky, the occasional deer.
Picnic tables sit near the parking area, so you can refuel after your hike. And if you’re into birding, binoculars are worth tossing in your bag.
7) Attend a Hartford Yard Goats baseball game
Baseball fans, you’ll want to catch the Hartford Yard Goats at Dunkin’ Park this week. They’re playing Binghamton on Sunday, May 18 at 1:10 pm EDT—a classic weekend outing.
The game features the Kids Run the Bases promotion, so after the final out, kids can dash around the diamond like pros.
This season’s a big deal—it’s the Yard Goats’ 10th anniversary. The promotional schedule is packed with giveaways and theme nights.
Friday nights are extra lively thanks to the “Baseball Night in America” theme. You get all the classic ballpark fun, plus some tasty food options (and no dishes to do).
Arrive a bit early to check out interactive tables and games. Some nights even have wellness resources and extra freebies.
8) Experience Avalon Nightclub in Uncasville
If you’re craving nightlife, Avalon Nightclub at Mohegan Sun is a solid bet. This place is known for world-class DJs and a killer sound system—seriously, the energy’s contagious.
Located right inside Mohegan Sun, Avalon’s easy to add to your evening plans. Expect a lively crowd and a party that keeps going late.
On Saturday, May 17, guests have raved about the DJ lineup and friendly bartenders. One person said they had “a blast” celebrating their 21st birthday, loving the music and service.
There’s an Albanian Night on May 30, too, if you’re thinking ahead. Events usually kick off around 6 PM.
Celebrating something special? VIP service is available and can make the night extra memorable. Dress code’s generally upscale-casual, so plan accordingly.
9) Take Backyard Adventure UTV Tours in Canaan
If you’re after an adrenaline rush and some fresh air, check out Backyard Adventure UTV Tours in East Canaan. You’ll drive state-of-the-art utility vehicles across hundreds of acres of private trails.
Tours start at $119 for an hour, with experienced guides leading the way. Bring a friend—extra passengers are $20 each, so it’s not a budget-buster for a group.
The Northwest Hills make a gorgeous backdrop as you tackle different types of terrain. It’s fun for beginners and more experienced folks alike.
They run tours from 9:00 am to 5:00 pm Monday through Wednesday, and probably similar hours the rest of the week. Best to call ahead and book.
When you’re done, maybe swing by Quarry View Golf Course or Land of Nod Vineyard and Winery to round out your day.
10) Join trivia nights across Connecticut bars
Looking for a fun way to flex your brain? Try out the trivia nights popping up all over Connecticut this week. McFairlawn Tavern and Kinsmen Brewing in the Waterbury area pull in regulars and newcomers with their weekly competitions.
If you’re around Fairfield, swing by Elicit Brewing on Monday, May 19th. Their pen and paper trivia in the beer hall is laid-back, with a great craft beer selection and a lively crowd.
Reverie Brewing in Newtown is hosting a 2000’s Music Trivia Night this week. If you know your Usher from your OutKast, it’s a good excuse to enjoy some local brews and maybe show off a little.
Every Wednesday at 7:30 PM, you’ll find Big Boy Trivia happening at Old Heidelberg Bar inside Graduate by Hilton New Haven. The spot’s right in the middle of New Haven, so it’s easy to fit into your plans.
Most of these places are cool with walk-ins, but if you want a table for your group, showing up 15-20 minutes early is smart. Trivia themes run the gamut from general knowledge to pop culture, and prizes usually mean gift cards or a free round.
Seasonal Travel Tips for Exploring Connecticut in May
May’s a sweet spot for exploring Connecticut—mild temps, blooming gardens, fewer crowds than summer. That said, the weather’s a bit unpredictable, so packing smart and having a transportation plan makes a big difference.
What to Pack for Spring Adventures
In May, Connecticut’s weather bounces between 50°F and 70°F, sometimes in the same day. Bring lightweight layers you can peel off or pile on as needed.
You’ll want a waterproof jacket—spring showers can show up out of nowhere. Comfortable walking shoes are a must if you’re planning to check out Connecticut’s many state parks.
Even on cloudy days, sunscreen, sunglasses, and a hat come in handy. The sun sneaks up on you, especially near the coast or when you’re out doing outdoor activities.
Bug spray? Bring it, especially for hikes or evenings. Ticks start showing up in May, so long socks and pants are a good call if you’ll be in the woods.
Navigating Transportation and Parking
Renting a car’s usually the easiest way to get around Connecticut. You’ll find all the big rental companies at Bradley International Airport and scattered around the state.
Public transit doesn’t cover much outside the cities. Metro-North Railroad runs from New York City up to towns like Stamford, Norwalk, and New Haven, but elsewhere you’re mostly on your own.
If you’re headed to busy spots like Mystic Seaport Museum, parking fills up fast on weekends. Try to get there before 10 AM or wait until after 2 PM for a better shot at a spot.
Many state parks start charging weekend parking fees in May ($15-$22 for non-residents). If you’re hitting a bunch of parks, a state park pass might save you a few bucks.
Planning Your Connecticut Itinerary
A rough itinerary helps you make the most of your Connecticut trip, but honestly, May’s weather can flip on a dime. It’s worth having a backup plan for rainy spells so you’re not stuck inside staring at your phone.
Mixing Indoor and Outdoor Activities
May usually brings temps between 55-75°F, but it’s all over the place some days. Try picking a main activity and a backup for each day—if it starts pouring, you’ll still have something to do.
Spring festivals are everywhere this month. They get crowded, though, so showing up before 10am will help you snag parking and skip the lines.
Mix things up—nature in the morning, museums in the afternoon. That way, if showers roll in, you’re already heading indoors. Here are a few combos to try:
- Morning: Gillette Castle State Park → Afternoon: Mystic Seaport Museum
- Morning: Hammonasset Beach walk → Afternoon: Yale Art Gallery
- Morning: Connecticut wine trail visit → Evening: dinner in Mystic
Accommodations Near Major Attractions
Staying in central spots cuts down on driving and keeps transportation costs in check. Mystic makes a great base for exploring eastern Connecticut—most major attractions are just a half-hour away.
If you’re heading west, New Haven or Hartford are smart picks. You’ll usually find weekend hotel rates that run 15-20% below the summer highs. Not bad, right?
Here are a few family-friendly places people seem to like:
- Mystic area: Water’s Edge Resort (right on the beach, and kitchenettes are a lifesaver)
- New Haven: The Blake Hotel (you can walk to Yale and plenty of restaurants)
- Hartford region: Avon Old Farms Hotel (close to tons of outdoor stuff)
Try to book at least three weeks ahead if you’re coming in May. Local vendor markets and events can draw crowds from all over, so rooms go fast.
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