Best Halloween Events in Connecticut 2025

The crisp air and scent of the fresh fall breeze signal the Halloween fun! In fact, from spine-tingling haunted trails to family-friendly events overflowing with apple candies and sugar pumpkins, the Constitution State again bustles with life this fall. Get ready to enjoy and experience the best Halloween events in Connecticut for 2025.

To reach these places, remember one important detail: your ride. Whether you’re heading to a lively party and need to avoid a DUI, or require a specialized vehicle, M7 provides the go-to transportation solutions. Moreover, their Non-Emergency Medical Transportation (NEMT) services ensure safe, reliable, and wheelchair-accessible rides so everyone can enjoy the season.

Pumpkins During Halloween Events in Connecticut 2025

1. Crawl-O-Ween ’25, New Haven

Brace yourself for the town’s biggest haunt! Crawl-O-Ween is the number one Halloween bar crawl. It’s also the largest party of its kind in the state. This massive event offers exclusive drink specials. Plus, cover-free entry to plenty of bars! Finally, it hosts a major costume contest. Experience unforgettable moments throughout this all-day, all-night affair.

2. The Trail of Terror, Wallingford

The Trail of Terror is one of Southern New England’s premiere haunted happenings. You absolutely shouldn’t miss it! Serious seekers of fright can take on the haunt scenes covering half of the four acres of forest. This season, the theme is Draw Your Fear — featuring a mysterious character called Seer. Dive into the unknown and uncover what he’s up to!

3. Haunting At The Ridge, Middlefield

The Haunting At The Ridge transforms your nightmares into reality! This mountain keeps its peace and happiness all year, except, of course, during Halloween. Whenever the season arrives, it turns into a place of horror. Ghouls and other monstrosities roam freely here. Make sure you’re prepared because you can’t turn back once you get in.

4. Pumpkin Patch Trolley Rides, East Windsor

Not everything needs to cause fear this Halloween. If you’re looking for a more wholesome outing, the Pumpkin Patch Trolley Rides are perfect for you! Ride on a trolley car and travel past beautiful fall foliage to the pumpkin patch field. There, each child gets to pick a free sugar-sized pumpkin. The museum campus offers more family-friendly activities. These include decorating pumpkins and playing in the corn box. Explore all the exhibits and displays for a visual delight!

5. Pumpkintown USA, East Hampton

Did you miss the hayride last year? Fret not because it’s back in Pumpkintown USA! You won’t need reservations either! This popular family destination always draws a smile to everyone with dozens of Pumpkinhead people and pets. You can find them in The Village and The Forest in over 17 settings! In addition, several scenes feature places like a firehouse, saloon, and post office.

6. The Pumpkin Passage at The Dinosaur Place, New London

Every Halloween season, New London’s Dinosaur Place becomes a magical world of lights, pumpkins, and friendly dinosaurs. This annual Pumpkin Passage event is designed for kids to enjoy marshmallow roastings, numerous family games, and an exciting Jurassic Jungle. Plenty of activities await adults as well, including live entertainers, food trucks, and great selfie and groufie spots.

Taking a Moment for Yourself

7. Connecticut Renaissance Faire, New London

Looking for medieval themed fun before all the big Halloween happenings? Look no further! The Connecticut Renaissance Faire gives you the best experience by letting you live out that fantasy. Enjoy jousting, music, comedy, and more! Let your kids play knights, see wizards and dragons, and even watch pirates and time travelers. Clearly, costume lovers need to be here!

8. Scarecrows Along Main Street, Wethersfield

You can celebrate Halloween at a chill and relaxing pace by strolling and admiring creative creations. Scarecrows Along Main Street offers the best opportunity to admire funny, artistic, and scary scarecrows. You and your companions are free to take selfies and group photos. You can also grab some lunch and do some shopping. Perhaps you’ll pick up something to take home with you.

9. Haunt on Eden, Southington

Another place for thrill seekers, Haunt on Eden promises screams with its frightening atmosphere and heart-pounding action! This year, the theme is Klowns ‘N Khaos Unleashed! Those brave enough to dive into this haunted experience of carnival carnage should be warned! Not for the faint of heart.

The M7 Advantage and Accessibility Edge

The spirit of Halloween should always create beautiful memories, even when you experience terrifying moments. But figuring out how to get to all the Halloween fun should be the last thing to frighten you.

M7 is Connecticut’s favorite ride around New Haven, Hartford, New London, and even Bridgeport.

We even provide trusted Non-Emergency Medical Transportation (NEMT) services, structuring it to assist seniors and individuals with special needs or mobility limitations for any trip. This means you get stress-free rides where everyone has the chance to join in. Ultimately, no one in the family is left out.

Ready to Ride? Book in Advance!

October opens the busiest season for Connecticut fall travel. Therefore, specialized vehicles demand high priority. Don’t leave your transportation to chance! Book online or through the app today to secure your Halloween trips.

Have a frightfully fun, and safe, Connecticut Halloween!

Best Halloween Events in Connecticut 2025