Fall Fun: Festivals & Other Weekend Activities | Newtown Moms

If you’re looking for something different to do this fall, here are a list of some great activities and festivals going on throughout our area this fall.


Fall Festivals: You can find many of these events on our calendar, in addition to a few other options that are a bit farther.


Saturday 9/7 & Sunday 9/8: 2019 St. Peter’s Apple Festival, Monroe
Time: Saturday 10AM – 5PM and Sunday 10AM – 4PM (rain or shine)
Don’t miss this annual tradition on the Monroe Green featuring 100+ vendors, food tent, live music, and kids’ activities.



Sunday 9/8: Savor Litchfield, Litchfield
Time: 1PM – 4PM
Savor Litchfield is the culinary event of the year with restaurants, bakeries, winemakers, distilleries, craft brewers, and more at South Farms. The event is for the whole family & features a kids zone & live music.


Saturday 9/14: 41st Annual Watertown Fall Festival
Time: 10AM – 5PM
Head to Veterans’ Memorial Park to enjoy tons of arts & crafts, food vendors, raffles, and entertainment for the kids.


Saturday 9/13 – October 27: Fall Festival & Corn Maze, Fair Weather Acres, Cromwell
Time: Fridays, Saturdays, and Sundays only, 10AM – 6PM
Tons of activities here for the whole family! Everything is included in the ticket price.


Saturday 9/15: Fall Celebration at Smyrski Farm, New Milford
Time: 8AM – 2PM
This family-friendly event is open to all and includes feathered hot-air ballon rides, free breakfast & lunch, farm animal petting zoo, hayrides, nature walks, and much more.


Saturday 9/15: Annual Ukrainian Festival at Castle Hill Farm, Newtown
Time: 11AM
The 44th Annual Ukrainian Festival kicks off at 11AM with Ukrainian style food, dancing, vendors, and more. Admission is by donation.


Friday 9/20: Sunday 9/22: Danbury Irish Festival, Portuguese Cultural Center, Danbury
Time: Friday 6PM – 10PM; Saturday 12PM – 11PM; & Sunday 12PM – 6PM
Live music all weekend, cultural events, a shopping village, and fun children’s entertainment


Friday  9/20 & Saturday 9/21: Milford Oktoberfest
Time: 12PM – 9PM (both days)
Head down to Fowler Field in Milford to check out this annual event. All proceeds benefit the Rotary Club of Devon.


Saturday 9/21 – Sunday 9/22: Newtown Arts Festival, Fairfield Hills, Newtown
Time: 11AM – 5PM (both days)
This festival was started by the Newtown Cultural Arts Commission to promote and support local arts in the community. This town-wide celebration includes all forms of creative expression.


9/29: Ridgefield’s Giant Pumpkin Weigh Off, Ballard Park, Ridgefield
Time: 10AM – 3PM
Sponsored by the Ridgefield Chamber, this annual event brings together pumpkin growers from all over the state competing for cash prizes for largest pumpkin, gourd, squash, and youth grower.


Friday 9/27: Fall Harvest Festival, Monroe Farmers’ Market
Time: 3PM – 6PM
Stop by the annual Fall Harvest Festival featuring live entertainment, a kids’ craft, a photo booth, and face painting.


Saturday 10/5: Fun-tober Festival benefiting Merryhill Daycare Center, Fairfield Hills, Newtown
Time: 10AM – 4PM
A fun day featuring fire trucks, police cars, other vehicles, Newtown Therapy Dogs, and much more!


Saturday 10/5: Apple Harvest Festival, Litchfield Historical Society
Time: 1PM – 4PM
Celebrate autumn and Litchfield’s 300 years of history. The event features an apple pie eating contest, colonial craftsmanship demonstrations, music, and food.


Saturday 10/5: REACHtoberfest, Castle Hill Farm, Newtown
Time: 6PM – 10PM
Annual event that raises funds for REACH Newtown’s youth programs. Tickets include live music, beer, wine tastings, and all you can eat from The Big Green Pizza Truck, Hog Wild BBQ, and Spud Truck.


Saturday 10/5: Litchfield County Harvest Festival
Time: 10AM – 4PM
Celebrate the season with local vendors and artisans will be there with fall favorites.


Saturday 10/12: 1st Annual Oktoberfest, Reverie Brewing Company, Newtown
Time: 12PM – 8PM
Celebrate Reverie’s 1st Annual Oktoberfest with live music, drink specials, and food trucks.


Weekend Activities: 

Castle Hill Farm Corn Maze, Newtown: Challenge your family by taking on the Corn Maze (opening 9/28) at Castle Hill Farm! After you can visit with the animals, take a hayride, pick your own pumpkin, and shop the farm stand.


Blue Jay Orchards, Bethel: In addition to picking apples, Blue Jay Orchards also features a great pick your own pumpkin patch, hayrides, and a country store.


Jones Family Farm, Monroe: Another great weekend option for the fall. Start your trip off with a visit to their winery and tasting room, then take a short drive up the road to their pick-your-own pumpkin patch. If you’re early enough in the season, you can even pick apples as well!


CT Wine Trail: There are a ton of picturesque spots along the CT Wine Trail a short drive away. Before going, check out the vineyard’s website for information on kid & pet friendliness, as well as your ability to pack a picnic.


Visit a CT Brewery: Breweries continue to pop up in our area, and the fact that we’ll soon have two in Newtown is a great excuse to gather with other families and enjoy a drink while the kids play. In addition to Reverie & the soon-to-open New Asylum, you can find more such as Charter Oak (Danbury), Broken Symmetry (Bethel), Housatonic River (New Milford), Kent Falls (Kent) or Nod Hill (Ridgefield).


Explore a new spot: If you have time and the weather is beautiful, take a ride to any of these place to explore a different part of CT: Gillette Castle, White Memorial, Kent Falls, or Wickham Park.


Know of anything else? Please share by emailing [email protected].

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