Connecticut’s got a wild mix of seasonal traditions, outdoor adventures, and cultural happenings that seem to change every week in September. Here’s a quick look at what’s going on around the state from September 21–27, 2025, so you can actually plan something fun. There’s a little of everything—history, food, music, nature—so you’re not stuck doing the same old thing.
You might wander through classic fairs, get your hands dirty with fall activities, or just enjoy some local performances. Each section points you toward a different vibe, so you can pick what actually sounds good to you.
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1) Guilford Fair
Check out the Guilford Fair from September 19–21, 2025, at the Guilford Fairgrounds. This is Connecticut’s second-oldest agricultural fair—started back in 1859—and it still celebrates farming traditions alongside all the modern stuff.
You’ll see livestock shows, craft displays, and agricultural exhibits. There’s also carnival rides, food trucks, and <a href="https://www.connecticutvisitorguide.com/attractions/theaters/hartford-stage-in-hartford-connecticut/”>live music across several stages. The fair really mixes rural roots with fun for all ages.
This year’s entertainment includes the Guilford Fair Family Circus and the Flying Wallendas, who are famous for their high-wire stunts. There are daily parades, tractor displays, and activities for kids, so it’s not just the same thing on repeat. The full Guilford Fair 2025 entertainment lineup is online if you want to see what’s happening when.
The crowds get thick, especially Saturday afternoons. Parking’s nearby, but traffic can slow you down. If you’re not into crowds, try coming early or late.
For hours, ticket info, or directions, check the Guilford Fair website. Saves you from scrambling last minute.
2) Shirefolk Weekend at Connecticut Renaissance Faire
Dive into Shirefolk Weekend at the Connecticut Renaissance Faire. It’s on September 20–21 and September 27–28 in Lebanon, so you’ve got two weekends to pick from. This fair’s been a fall staple for almost 30 years.
The Shirefolk theme is all about simple joys—hearty food, games, silly contests. It’s got a halfling village vibe, meaning lots of chances to eat, drink, and just hang out.
Besides the theme, there are 100+ artisan vendors, live music, comedy, and jousting tournaments. Performers like the Harp Twins bring the medieval mood to life.
Crowds swell in the afternoons, especially when big acts hit the stage. If you want a quieter experience, show up early. Food lines can drag, so maybe stash a water bottle and snacks.
It’s a mix of themed fun and classic Renaissance Faire stuff—works for families, friend groups, or if you’re just rolling solo.
3) Lobster Roll Festival
Milford’s first Lobster Roll Festival lands Saturday, September 20, 2025, at Walnut Beach. It goes from late morning into the evening, so you can squeeze it in whenever.
Food is the star—vendors serve up warm, buttered lobster rolls, a Connecticut shoreline classic. Local breweries and wineries add some drink options to the mix.
Live music keeps things lively on the sand, with bands like Mystic Bowie’s Talking Dreads playing sets. So you can eat, wander, or just chill to the music.
Bringing kids? There are activities for them too, like art projects with The Giggling Pig. Gives the little ones a break from the food tents.
Parking at Walnut Beach fills up fast on weekends. Arrive early or look for lots within walking distance.
More details—times, vendors, music—are on the Milford Regional Lobster Roll Festival page or the Walnut Beach Association event listing.
4) Corn Maze Adventures
This week, Connecticut’s corn mazes are open across the state. Each one’s got its own theme and level of challenge, so pick whatever matches your mood—quick stroll or a real puzzle.
Bishop’s Orchards in Guilford has a 3.25-acre corn maze themed around New Haven pizza this year. The design changes every season, so it’s never quite the same. Grab some fresh produce or baked treats while you’re there.
Lyman Orchards in Middlefield offers a big corn maze and cider donut festival on September weekends. Walk the maze, then grab food, listen to music, or join some family activities. Saturdays get busy, so budget extra time.
Want something low-key? Fort Hill Farms in Thompson has a corn maze adventure open daily through early November. They focus on wellness and nature, plus you can check out their gardens or creamery.
If you’re into puzzles, Corn Maze CT adds trivia games along the way. Makes it more than just a walk through the corn.
5) Visit The Warrens’ Occult Museum
The Warrens’ Occult Museum in Monroe, once tucked under Ed and Lorraine Warren’s house, is back open. It’s packed with oddities from their decades of paranormal investigations. The Annabelle doll’s probably the most famous item, but there’s plenty more for anyone curious about the supernatural side of Connecticut.
After closing in 2019, the museum reopened under new ownership—comedian Matt Rife bought the place and now runs guided tours and overnight stays. You get to see the creepy artifacts up close and learn about the Warrens’ legacy in American paranormal lore.
Overnight stays sell out fast, so if you’re thinking about spending the night, book ahead. All the info—pricing, availability—is at the Warrens’ Occult Museum overnight stays.
The vibe here isn’t for everyone. Some folks find it a little too intense, and the stories behind the objects are pretty wild. But if you’re into history with a side of the paranormal, it’s a unique stop.
6) Kayaking in Collinsville
Launch right onto the Farmington River from the ramp next to the shop. The water’s calm, perfect for beginners or anyone just looking to relax. If you want a workout, paddle upriver and burn off some energy.
Collinsville Canoe & Kayak rents kayaks, canoes, and paddleboards. Staff hand you a life jacket and paddle, help you get set up, and you’re off. The whole process is pretty quick, even on busy weekends.
The main route runs about a mile and a half upriver, then you drift back down. It’s enough for a workout but not so far you’ll regret it. You’ll see plenty of other paddlers, especially if the weather’s nice.
Their shop has loads of paddling gear. If you catch the bug, you can compare rentals to buying a boat, new or used.
Parking’s a pain on sunny afternoons—try to get there early. Afterward, wander into Collinsville for coffee or a snack. Makes for a solid half-day out.
7) Biking on Collinsville Paved Trail
Take a spin on the paved trail in Collinsville for an easygoing bike ride. It links up with the Farmington River Trail, so you get water views and quick access to the town center.
The surface is smooth, so it works for road bikes, hybrids, or families with kids. The ride’s pretty gentle—mostly flat with some curves, nothing too crazy.
Parking’s simple near the trailheads, and you can stop in Collinsville for a coffee break or snack. The Collinsville trail maps show different entry points, so you can pick your own distance.
It gets busy on weekends, but mornings or weekdays are much quieter.
This trail isn’t super long compared to the Farmington Canal Heritage Trail, but it’s a solid option if you want something short and easy without leaving town.
8) Farmington River Tubing
Float down the Farmington River in New Hartford on a tubing trip that covers about 2.5 to 3 miles, with some mellow rapids and calm stretches.
Start at Satan’s Kingdom Recreation Area off Route 44. You check in, grab your tube, and catch a shuttle upriver. The float usually takes around two hours, give or take depending on the river’s flow.
Farmington River Tubing provides sturdy tubes and includes a life jacket with every rental.
The water stays cold, even in late September—dress for it, and bring water shoes since the rocks are slippery.
This is best for people comfortable in moving water. There are minimum age and height rules, so check before bringing younger kids.
Weekdays are way less crowded than weekends. Parking’s limited, so arrive early if you want a spot.
9) Brown’s Harvest Fall Festival
Spend a weekend at Brown’s Harvest in Windsor. The festival runs every Saturday and Sunday, September 20 through November 2, 2025, from 10 AM to 5 PM (last entry at 4 PM).
There’s a 5-acre corn maze with a new theme every year, plus a smaller one for the kids. Families usually start with a hayride or barrel train, then hit the play areas. Don’t forget socks for the jump pad—it’s only open if the weather cooperates.
Food-wise, you’ve got cider and baked goods. Seating’s outside, so bring a jacket if it’s chilly. October weekends can get crowded, so expect some lines.
Admission covers most things, but you might want extra cash for snacks or pumpkins. If you’re coming back a lot, Brown’s Harvest now has season passes.
They’ve been running this festival for 47 years, and it still draws a good crowd. It’s a nice way to get your fall fix without leaving Hartford.
10) Live Music Events in Hartford
Hartford’s got some decent live music options this week, from small jazz jams to bigger concerts. Venues across the city host both touring acts and local bands, so there’s variety.
Jazz fans can check out the Hartford Jazz Society Saturday Afternoon Jazz Jam at Café Nine. The lineup rotates, so you never really know what you’ll get—but it’s always got that community vibe.
For bigger shows, peek at Hartford.com and Eventbrite’s Hartford calendar. You’ll find everything from regional favorites to national tours.
Crowds are usually smaller than in big cities, so you can get pretty close to the stage. Some venues fill up fast, though, so it pays to arrive early.
Whether you want a laid-back bar or a ticketed concert, Hartford’s music scene has something going on this week.
Planning Your Connecticut Adventure
When you’re out exploring Connecticut in late September, you’re juggling cultural stuff with outdoor fun. Just be ready for unpredictable weather, a packed calendar, and the usual shuffle between towns and cities.
Tips for Making the Most of Your Week
Try planning your days by grouping nearby spots together. If you’re heading to a coastal town, maybe hit up a museum or local market in the same area instead of zigzagging all over the state. It’s just easier and lets you actually enjoy what you see, rather than spending half your trip in the car.
For popular attractions—think theaters, casinos, or those big September fairs—grab your tickets online ahead of time. These places fill up fast, especially on weekends. Booking early not only guarantees your spot but also locks in the price, which is honestly a relief when you’re budgeting.
In bigger cities like New Haven or Hartford, public transit can be a lifesaver. Parking downtown is usually a hassle, and trains or buses tend to run on time. In smaller towns, though, you’ll probably want a rental car for the freedom.
Don’t pack your evenings too tight. Sometimes weather or traffic throws off your daytime plans, so it’s smart to leave wiggle room. Keep a few backup ideas handy—maybe a casual spot for dinner or a local brewery—so you can switch things up without stress.
Weather and Packing Considerations
Connecticut’s September weather is all over the place. One afternoon it’s in the low 70s°F, but by night, you might need a jacket with temps dipping into the 50s. Layers are your friend—no need to lug around heavy clothes, just something you can throw on or peel off.
A lightweight rain jacket or small umbrella comes in handy. Coastal showers pop up out of nowhere, and if you’re hiking, waterproof shoes are a smart pick since trails get slick.
If you’re heading to an outdoor festival or fair, go for comfy shoes. You’ll spend plenty of time walking over grass or gravel, and sandals just don’t cut it. A small backpack works for carrying water, snacks, or an event guide—nothing fancy.
The sun goes down earlier as September rolls on. If you’re sticking around for evening events, a flashlight or your phone’s light helps. Nights get chilly, so toss a sweater or fleece in your bag just in case.
Navigating Connecticut’s Local Culture
Connecticut’s culture really comes alive through its seasonal events and food. There’s a blend of history, hometown pride, and local flavor that gives the state its personality—something you’ll notice pretty quickly if you’re paying attention.
Seasonal Events and Traditions
September is prime time for fairs and festivals. Agricultural fairs are everywhere, with livestock shows, prize vegetables, and old-school crafts. The Durham Fair is a classic—farming still runs deep here, and these events prove it.
Music and the arts pop up all over, too. Places like the Westport Playhouse or small community theaters host performances that are easy to catch and rarely disappoint. Outdoor concerts and town green meetups bring everyone together, locals and visitors alike, for a laid-back vibe.
If you’re drawn to the big stuff, the Big E just over the border in West Springfield, Massachusetts, is a huge draw for Connecticut folks. It’s a mashup of statehouse replicas, food stands, and carnival rides. Yeah, it gets packed, but it’s a wild, fun way to get a taste of New England’s mix.
Coastal towns do their own thing, too. Oyster festivals—like Norwalk’s—mix seafood, live music, and a bit of local pride. You’ll get a real sense of how much the Long Island Sound means to people here, and honestly, it’s hard not to get swept up in the energy.
Dining and Culinary Experiences
Food in Connecticut draws from New England roots and a mix of immigrant flavors. You’ll spot clam chowder, lobster rolls, and apple cider donuts at local stands—especially when September rolls around. Fairs and roadside markets seem to love these classics.
Pizza here? It’s a big deal, especially in New Haven. The thin crust and coal-fired ovens set it apart from the New York or Chicago stuff. People line up for ages at the famous places. Is it worth it? Most folks would say yes, at least once.
Farm-to-table spots have popped up all over. In Litchfield County and along the Connecticut River Valley, restaurants usually grab their produce from nearby farms. Menus shift with whatever’s growing, so you’ll probably see squash, apples, and late corn in early fall.
Craving something different? Cities like Hartford serve up Polish and Puerto Rican dishes, while Bridgeport leans into Portuguese and Brazilian flavors. These neighborhoods let you dig into meals that go way beyond the usual New England lineup.
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