All Weekend 

Harvest Festival Weekend at Stamford Museum and Nature Center (Fairfield County) 
Something for all ages including pumpkin carving, scarecrow contest, face painting, animal demonstrations and hayrides. Costumes are welcome and you can wear them in the daily parade. Several food trucks will be on hand, and Friday night is an adults only Oktoberfest event with fun, food and beer. Tickets can be purchased ahead of time online. 
Saturday-Sunday. Members $5; non-members $10; under 3- free.

Tower Toot at Heublein Tower in Simsbury (Hartford County) 
Hike 1.5 scenic miles up to the tower. ​This free festival offers German music, face painting and a meeting with Smokey the Bear. This is a moderately difficult hike; I would recommend for 4 and up. The views from the top are breathtaking, especially with the fall foliage. Parking at this event can be very difficult along Simsbury Road, so plan ahead and arrive early.
Free.

Haunted Mini Golf in Farmington (Hartford County) 
The course is transformed into a Halloween horror show including a haunted graveyard, dracula's fountain and other spooky sights. Halloween treats and prizes are available at the ice cream parlor. Some decor may scare little ones, so use your discretion. 
Thursdays-Sundays through Oct. 27. $10 per person. 

Glastonbury Apple Harvest Festival (Hartford County) 
Awarded "Best Festival" in Hartford Magazine this year, so see if it lives up to the reputation! Live music, craft booths, a baking contest, rides, games, animals and more. Tons of apples and apple treats for sale, and a 5K, 1K and kids race to burn off some calories. 
Friday through Sunday. Friday- free; other days $5 per person and under 3 free.

Shoreline Oktoberfest in Guilford (New Haven County) 
Three days of Germany-style fun and food for all ages at the Guilford Fairgrounds. Live music and dancing, authentic German food and beer, rides, games, and plenty of kids' activities. Enjoy the pumpkin patch, petting zoo, and weiner dog races. If you indulge in the beer, please don't drink and drive. Cabs will be available at the end of the event. 
Friday-Sunday. Adults - $12; ages 15 and under - free. Save money by purchasing advance tickets online. 

Saturday, October 19 

Great Pumpkin Festival in Putnam (Eastern CT) 
Live music, movies, crafts and pumpkin-flavored tastings are among the free activities at this town wide celebration. Take a 90-minute train ride through beautiful northeastern CT and participate in the scarecrow contest. 
Free. Train Ride is $25 and tickets may be purchased ahead of time.

Old Greenwich School's Pumpkin Patch (Fairfield County)
Come and enjoy this fall festival with plenty to offer for the kids. Haunted house, bouncy houses, hay maze, games and much more. This is the school's major community event and fundraiser.  
Free. 

Trumbull AgriScience Halloween Festival (Fairfield County) 
Celebrate Halloween on the farm with fun activities such as tractor rides, petting zoo, spooky science lab, food and a ton of pumpkins to choose from. 
$5 per person. 

Thomas Hooker Day Parade in Hartford (Hartford County)
Downtown Hartford is the place to be for this very spirited parade. Mardi gras beads and candy will be flowing in this celebration of the city and the creative people who call it home. Come enjoy the after party at Black-eyed Sally's when the parade finishes. 
Free.  

Enchanted Forest Candlelit Walk in Sharon (Litchfield County) 
This non-scary program is geared towards children under 8. You'll stroll through the forest, meet costumed animals and learn how real animals live in the wild. The tour concludes with hot chocolate and a hayride. 
$4 per person.

Sunday, October 20 

Fall Foliage Cruise in Haddam (Central CT)
All aboard for a perfect fall day on the Connecticut River. You'll cruise along and see peak foliage, maybe some bald eagles, and landmarks such as the Goodspeed Opera House and Gillette Castle State Park. Your captain and crew will narrate about history and terrain. These sell out quickly, so don't miss out! 
Adults - $20; Children - $15

The Laurie Berkner Band in Stamford (Fairfield County) 
This highly-successful and beloved children's recording artist comes to the Palace Theater for an afternoon show. The kids will love seeing her and the band live after listening to the CD in the car for hours! 
$30 and up.

Fall Foliage Hike at Sleeping Giant State Park in Hamden (New Haven County) 
If you aren't into the cruise idea, head out to one of the most beautiful state parks to view leaves. This is a rugged, three-hour hike and participants should be in good shape. You'll navigate through rocky, uneven terrain at times. Pack snacks and water, and no pets please. Use judgment as to how old your child would need to be to last the entire time. 
Free. 

For other ideas on how to enjoy the season, check out our post on pumpkin patches in Western CT.

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Have a beautiful fall weekend!