Inspiration

Classic Fall Activities to Enjoy with the Family in Eastern Connecticut

last updated: October 2026

From corn mazes and apple picking to colorful scarecrows and classic fall treats, Eastern Connecticut is a wonderful destination for enjoying autumn with the whole family.

When there is a crisp chill in the air and the leaves begin turning beautiful shades of red, orange, and yellow, it is the perfect time to get outside and enjoy a classic Connecticut fall day. Whether you are looking for an afternoon of family fun, a trip to the orchard, or a festive fall tradition, there is something for everyone to enjoy.

Preston Farms Corn Maze

Looking for a classic fall activity that the whole family can enjoy? Head to Preston Farms Corn Maze for an affordable day filled with fun and adventure.

Make your way through the maze while searching for 16 stamps hidden throughout the paths. If you do not find them all during your first visit, there is no need to worry. You can return for free and finish the maze by bringing your stamp card with you.

For an extra challenge, Preston Farms also offers flashlight mazes. Bring your own flashlight and see how well you can navigate the maze after dark.

Throughout the month, keep an eye out for special events featuring food trucks, bonfires, and live music. With plenty to explore, Preston Farms is a great place to make an afternoon or evening of your fall adventure.

Holmberg Orchards, Gales Ferry

Nothing says fall quite like spending a day at the orchard, and Holmberg Orchards in Gales Ferry is a great place to enjoy one of Connecticut's classic autumn traditions.

Bring the family and search through the orchard for the perfect apples to bring home. After picking your apples, take some time to explore the farm and find the perfect pumpkin to bring home for Halloween.

Of course, no trip to the orchard would be complete without enjoying some delicious treats from the farm stand. Pick up something sweet to enjoy during your visit or bring home for later.

Visiting on the weekend? Saturdays and Sundays also offer free hayrides, making a trip to Holmberg Orchards even more fun for the family.

Scarecrows in the Village at Olde Mistick Village

For a unique fall tradition, head to Olde Mistick Village for Scarecrows in the Village.

Each year, the village transforms into a festive fall destination as the shops create their own handmade scarecrows. Take a stroll through the village and see the creativity that goes into each one.

As you explore, you can participate in the community tradition by voting for your favorite scarecrows. QR codes are posted throughout the village, making it easy to cast your vote in the different categories.

It is a fun way to spend an autumn afternoon while exploring the shops, enjoying the scenery, and seeing all the creative scarecrow displays.