Fall into Fun: Upcoming Events in Stafford, CT this Autumn

By Brian Goepfrich, Events & Celebrations Committee

As summer gently fades and the Stafford landscape begins its quiet transformation to golden and orange hues, the town comes alive with anticipation for a season rich in community spirit, festive traditions, and family-friendly fun. Though small in size, Stafford is overflowing with charm, and this fall, the calendar is brimming with events that highlight exactly why so many are proud to call this place home. 

If you haven’t already marked your calendar, here’s your guide to some of the most anticipated events happening around town this season: 

Farm Day – September 6–7, 2025

With over 300 years of rich agricultural history, Stafford’s farming roots run deep and every September, we celebrate that legacy with Stafford Farm Day, the town’s largest agricultural event. Held along historic Stafford Street and hosted by Foster Hill Farm, Witt Farm, and Tripple T Family Farm, this beloved tradition brings together families, farmers, and friends for a weekend of hands-on fun and community connection. 

Farm Day is more than just an event, it’s a celebration of the people and practices that continue to shape our town. From agricultural displays and demonstrations to kids’ activities, farm tours, live entertainment, and local food and craft vendors, there’s something for everyone to enjoy. You’ll meet local farmers, explore animal exhibits, and learn about the importance of supporting local agriculture. 

Organized entirely by volunteers and sponsored by the Stafford Agricultural Commission and the Rotary Club of Stafford, Farm Day is a grassroots effort with a big impact. Funds raised support future agricultural initiatives in town, including scholarships, a community garden, and the dream of a community farm store. 

Whether you’re a lifelong resident or a first-time visitor, Farm Day is a true hometown tradition, a joyful way to close out summer and celebrate the heart of Stafford. 

Main Street Music Series – September 12, 2025

Join us for a soulful evening of live music at Arts on Main Street’s Music Series, featuring the talented Six Pack of Blues Band on Thursday, September 12, 2025, at Haymarket Commons on Main Street. Set against the charming backdrop of downtown Stafford, this free community event promises a night of wonderful music, great vibes, and local connection. Bring a chair or blanket, grab a bite from nearby eateries, and enjoy the smooth sounds of blues under the early autumn sky. It’s the perfect way to unwind and celebrate the arts in the heart of Stafford. 

Applefest – September 27, 2025 

Celebrate the season’s most iconic fruit and the creative spirit of our town at Stafford AppleFest, held across Haymarket Common, Hyde Park, and Main Street. This beloved annual event transforms the heart of Stafford into a festive autumn wonderland, perfect for a day of apple-filled fun. 

Wander through rows of artisan vendors and handcrafted goods, enjoy live music, and treat yourself to homemade seasonal baked goods and fall-inspired food and drinks. Kids and families will love the interactive activities, while apple pressing demonstrations offer a glimpse into traditional New England charm. 

Don’t miss the Grace Episcopal Church’s famous apple pies and apple crumb, along with hearty soups and warm lunch options to keep you cozy throughout the day. 

Whether you're a die-hard apple lover or simply looking for a fun way to spend a fall afternoon, Stafford AppleFest offers something for everyone, and it’s one of the many reasons this town feels like home. 

Bosco Fowler Memorial 5K– September 28, 2025 

Hosted by the Rotary Club of Stafford, this annual race honors a local legend and brings runners and walkers together for a great cause. Whether you're racing for time or just enjoying the route, it’s a wonderful way to support the community. Come run, walk, or just cheer on others at the Stafford School Complex.  

Scarecrow Competition – Hosted by the Stafford Garden Club 

Get ready to roll up your sleeves and let your creativity shine! The Stafford Garden Club invites local businesses, organizations, and community groups to take part in the annual Scarecrow Competition, a beloved fall tradition that brings color, character, and a touch of whimsy to Main Street all October long. 

Participants are encouraged to design and build their own unique scarecrows; funny, spooky, clever, or classic, and display them proudly for the entire town to enjoy. It’s a fantastic way to show off your team spirit, celebrate the season, and be part of a community-wide showcase of imagination and autumn charm. 

Whether you're crafting a scarecrow for the first time or returning with a new idea, this is your chance to be part of a festive tradition that makes Stafford feel like home. Voting for your favorite scarecrow will occur at Trick or Treat on Main Street.  

Stafford Speedway – Final Race of the Season NAPA Auto Parts Champions Night: October 3 

When race night rolls around in Stafford, you can feel it before you even get to the track, the low, steady rumble of engines echoing through town, a sound that signals something special is happening. That unmistakable buzz will reach its peak on Friday, October 3, as Stafford Speedway hosts the Final Race of the Season: NAPA Auto Parts Champions Night. It’s more than just a race, it’s the grand finale of a thrilling season, where champions are crowned and the roar of the crowd matches the thunder of the track. Whether you're a die-hard fan or just love the energy that fills the air, this night is a celebration of speed, skill, and Stafford’s deep-rooted racing tradition. Don’t miss your chance to be part of the excitement as the engines fire up one last time in 2025! 

Halloween Home Decoration Contest 

Show off your spooky spirit in Stafford’s Halloween House Decoration Contest 2025 by transforming your home into a haunted masterpiece! This fun and festive competition invites residents to get creative and compete for three exciting awards: People’s Choice, determined by online community votes; Scariest House, judged on spine-chilling impact; and Best Theme, awarded for the most cohesive and imaginative display. To participate, submit your name, address, and a brief description of your decorations by October 29, 2025. Once entered, a member of the Events and Celebrations Committee (ECC) will follow up with judging details. Whether you're aiming to terrify, impress, or simply entertain, this is a great way to celebrate Halloween and connect with the community. For questions, email events@staffordct.org. 

 Trick or Treat on Main Street – October 25, 2025 

 Get your costumes ready and bring the whole family to downtown Stafford for one of the most anticipated events of the season, Trick or Treat on Main Street! On Saturday, October 25, 4:00 PM -6:00 PM, Main Street transforms into a safe, walkable Halloween wonderland where local businesses and organizations hand out candy and treats to costumed kids of all ages. This beloved community tradition is a fun and festive way to celebrate Halloween, complete with decorated storefronts, spooky surprises, and plenty of photo-worthy moments. Whether you're a little ghost, superhero, or pumpkin princess, there's something magical about seeing Main Street come alive with Halloween spirit. 

Don’t miss this chance to enjoy a night of sweet treats, community connection, and fall fun in the heart of Stafford! 

With so many exciting events happening this fall and likely even more popping up around town, there’s no shortage of ways to celebrate the season in Stafford. From festive traditions to community favorites, there’s something for everyone to enjoy. Have fun, be safe, and take time to appreciate this amazing community we’re lucky to call home.

Happy Fall, Stafford!