Pumpkins, Pirates, And Haunted Trails: Here’s What’s Happening Across CT This Weekend

CONNECTICUT — October is in full swing, and Connecticut is showing off its festive side with a weekend packed with music, food, and spooky thrills. From pumpkins and witches to pirates and haunted trails, the Oct. 17–19 weekend has something for every kind of fall fan — whether you’re chasing carnival lights or Halloween chills.

Step right up for family fun at the Cove Side Carnival in historic Wethersfield, running Oct. 17–19. This waterfront carnival features classic rides, midway games, live music, and plenty of fair food favorites. The event brings a nostalgic small-town vibe to one of Connecticut’s oldest towns, making it a perfect weekend stop for families and thrill-seekers alike.

Downtown Putnam transforms into a fall wonderland on Saturday, Oct. 18, for the Great Pumpkin Festival. This annual celebration features hundreds of pumpkins on display, along with food trucks, live music, hayrides, a craft fair, and, of course, giant pumpkins. Local shops and restaurants join in on the fun.

Music lovers will want to head to Farmington on Saturday for the 10th Annual Farmington Valley Acoustic Festival at Winding Trails. The outdoor event showcases singer-songwriters and acoustic acts from across New England. Bring a blanket, grab some local eats, and enjoy a relaxing afternoon surrounded by nature and harmonies.

For something truly magical, check out the 4th Annual Witch Paddle in Milford on Saturday, Oct. 18. Dozens of paddleboarders dressed as witches (and a few warlocks) will take to the water for a bewitching paddle around the harbor. It’s a unique and photogenic event that’s part Halloween spectacle, part outdoor adventure. Be sure to dress your part.

The spooky storytelling series West Hartford Hauntings continues this weekend (Oct. 16–25) with costumed guides leading lantern-lit cemetery tours. Hear chilling — and true — tales of the town’s past as actors bring local history to life. It’s spooky, educational, and one of the most beloved Halloween traditions in the Hartford area.

If you’re ready for a real fright, Brookfield’s Scarrybrooke Park Haunted Trail (Oct. 11–25) promises a night of screams and surprises. This long-running haunted attraction winds through Harrybrooke Park with new scenes and scares every year. Proceeds benefit local charities — so you can feel good about being scared out of your wits.

Mystic Seaport Museum dives into the dark side with What Lurks Beneath (Oct. 17–26), an immersive Halloween experience that blends maritime lore with eerie storytelling. Guests explore the museum grounds after dark, encountering ghostly sailors and mysterious sea creatures along the way. It’s a uniquely nautical spin on Halloween that’s perfect for adventurous spirits.

If you’d rather skip the scares and savor the flavors, the Culinary Carnival at Stone Acres Farm in Stonington (Oct. 19) offers a farm-to-table celebration of local food. Hosted by the Yellow Farmhouse Education Center, the event features chef demos, tastings, and live music — all set against the backdrop of a historic working farm.

Avast, ye theater lovers! Salt Marsh Opera presents The Pirates of Penzance at The Kate in Old Saybrook on Oct. 17 and 19. The Gilbert and Sullivan classic brings humor, heart, and high-seas hijinks to the stage. Whether you’re a die-hard light opera fan or just in it for the laughs, it’s a delightful cap to a weekend of adventures.

From witches on paddleboards to garlic-laced harvest treats, from glowing lantern tours to pirates belting out sea shanties, Connecticut is bursting with creativity and community this October weekend. Grab your cozy sweater, charge your phone for photos, and set out for a fall weekend you won’t forget.