From apple orchards to pumpkin patches, explore the top fall festivals and community celebrations happening across Connecticut this season.

Autumn in Connecticut is a season filled with color, community, and celebration. From apple harvests and pumpkin festivals to live music and family activities, there’s something happening in nearly every town this October. Whether you’re planning a weekend day trip or looking for local fun close to home, here are some of the best fall festivals to explore this season.

October 3–5 & 10–12 — Southington Apple Harvest Festival

Southington, CT
One of Connecticut’s largest and most beloved fall events, drawing nearly 100,000 visitors each year. Enjoy live entertainment, a parade, craft vendors, and the Apple Harvest Road Races on October 5.

October 4 — East Hartford Fall Festival

East Hartford Town Green
Kick off the month with a full day of food trucks, local vendors, children’s activities, and live entertainment on the Town Green.

October 4 — Easton Paws & Pumpkins Festival

Easton, CT
A favorite for families and dog lovers alike. Enjoy food, bingo, craft beer, pumpkins, and plenty of kid-friendly and pet-friendly activities.

October 4–5 — St. Francis Family Fun Carnival

Weston, CT
This community carnival has something for everyone—rides, games, food, and entertainment—all hosted by St. Francis of Assisi Parish.

October 10–12 — New Canaan Nature Center Fall Fair

New Canaan, CT
Celebrate fall with pumpkins, hay mazes, apple games, music, rides, and the always-popular Spooky Stroll.

October 10–12 — Milford Pumpkin Festival

Downtown Milford
A weekend of small-town charm, kicking off Friday evening and continuing through Sunday with live entertainment, food, crafts, and community fun.

October 10–12 — Salisbury Fall Festival

Salisbury, CT
The entire town comes alive with crafts, food, and children’s activities at this scenic Litchfield County event celebrating all things autumn.

October 11 — Prospect Pumpkin Festival

Prospect, CT | 4–8 PM (Parade at 5:45 PM)
Now in its 21st year, the Prospect Pumpkin Festival offers local vendors, food, live entertainment, and a festive evening parade.

October 11–12 — Connecticut Garlic & Harvest Festival

Bethlehem, CT
A unique favorite featuring garlic-inspired cooking demos, live music, lectures, vendors, and plenty of garlic-themed foods and crafts.

October 12 — Washington Harvest Festival

Washington, CT | 12–5 PM
Live music, vendors, kids’ games, train rides, scarecrow contests, and small-town fun fill this community celebration.

October 17–19 — Glastonbury Apple Harvest & Music Festival

Glastonbury, CT
One of the state’s signature fall festivals with amusement rides, a 5K road race, live music, and plenty of local food and crafts.

October 18 — Putnam’s Great Pumpkin Festival

Putnam, CT
Downtown Putnam transforms into a pumpkin-themed celebration with live music, crafts, boutiques, and family-friendly entertainment.

October 18 (Rain Date Oct 19) — Pumpkin Festival at Boothe Park

Stratford, CT
A Fairfield County favorite featuring pumpkin displays, food trucks, crafts, and activities set within the historic Boothe Memorial Park.

October 18–19 — Mystic Apple Festival

Olde Mistick Village, Mystic, CT
Celebrate apple season with local vendors, apple and pumpkin goods, live music, and family activities in one of Connecticut’s most charming villages.

October 25 — Ivoryton Village Pumpkin Festival

Essex, CT
A festive evening event with a pumpkin carving party, costumes, and illuminated displays that bring over 1,500 visitors to town.

October 25–26 — Mohawk Mountain Fall Festival

Cornwall, CT
Enjoy hay rides, pumpkin painting, inflatables, food trucks, and a Makers Market—all set against the stunning fall backdrop of Mohawk Mountain.

October 26 — Trumbull Fall Festival

Trumbull, CT | 10 AM – 2 PM
Lawn games, pumpkin decorating, crafts, fire truck displays, face painting, and food trucks make this a great family outing.

Through Early November — Pumpkintown U.S.A.

East Hampton, CT
One of Connecticut’s most whimsical fall attractions, featuring the famous Pumpkinhead figures, scenic hayrides, and the family-friendly Pumpkin Village.

November 1–2 — Lyman Orchards AutumnFest

Middlefield, CT | 10 AM – 4 PM
Wrap up the fall festival season with a weekend of apples, cider, seasonal foods, and local vendors at the Apple Barrel Market at Lyman Orchards.

Explore Connecticut This Fall

From the shoreline to the hills, each festival celebrates what makes Connecticut’s towns so special—community, creativity, and connection. As you enjoy these events, remember that fall is also a beautiful time to explore new neighborhoods and dream about your next move.

Because home is more than a place—it’s a community.

— The Fowler Sakey Team, Coldwell Banker Realty