There’s nothing to get you in the autumn spirit quite like picking your own pumpkins. Whether it’s a fun way to spend a Saturday with your kids, an excuse to hang out with your friends or the key to making that perfect jack-o’-lantern, going to a farm to pick your own pumpkins is a beloved tradition. Pumpkin-picking season starts in mid-September and lasts through November. Here are some options in the Chesapeake area.
Horsmon Farm | St. Leonard
Celebrating its 100th anniversary in 2025, Horsmon Farm has been owned by the same family for four generations. It was once a tobacco farm but now focuses on raising cattle and pigs, as well as growing crops.
The farm is open to visitors in September and October, when guests can pick their own pumpkins and mums from its fields, go on a hayride or try to solve its corn maze. As an agricultural education destination, Horsmon Farm is also open to private visits and parties throughout the year. Guests can meet friendly farm animals, go fishing in the pond and even learn about the work that area farmers are doing to preserve the local environment. horsmonfarm.com
Family Affair Farm | Easton
Family Affair Farm might be best-known for its u-pick berries, which are available during the summer. After berry season is over, though, the farm closes temporarily before reopening for the fall harvest. During its annual Fall Festival, Family Affair Farm boasts a large pumpkin patch with a variety of different pumpkins to choose from, as well as a “Field of Fun” play area for children.
The crown jewel, though, is the massive 4-acre corn maze that is erected on the farm’s property every year. Truly daring explorers can take on the maze during “Flashlight Nights” on Friday and Saturday evenings, when visitors can explore the corn maze with nothing but the light from a flashlight to guide them. familyaffairfarm.wixsite.com
Kent Fort Farm | Stevensville
Located on the southern tip of Kent Island, Kent Fort Farm offers a no-frills pumpkin picking experience and is a great place to stop by if you’re visiting the island. During the summer, the farm has u-pick peaches, berries and vegetables. Then, on weekends in October, the farm offers “all-you-can-carry” pumpkin picking, where visitors pay a flat fee for as many pumpkins as they’re able to carry to the hayride from the pumpkin patch. For younger children and animal lovers, the farm also has a petting zoo. facebook.com/kentfortfarm
Councell Farms | Easton
Councell Farms was founded in 1981, but the Councell family has been farming in Talbot County since 1690. The farm opens to guests in September and October, with its “Field of Fun” attractions serving as popular fall staples for local families. In addition to picking pumpkins, visitors can also feed farm animals, explore the farm’s corn maze, go down a slide built out of a combine tractor and more.
Councell Farms also sells locally-sourced apples and fresh apple cider during the fall. Visiting The Creamery at Councell Farms is a must if you’re looking for a sweet treat at the end of the day. councellfarms.com
Y Worry Farm | Davidsonville
Y Worry Farm has been a destination for Anne Arundel County families looking for fall and Halloween decorations for more than 35 years. The pumpkins in the pumpkin patch are still on the vine and range from tiny “baby” plants to huge ones that require wagons to transport. If you’re looking to diversify your fall decor, the farm also has different kinds of gourds, winter squashes and Indian corn.
There are also plenty of fun attractions for children and families, including a climbable straw pyramid and a teepee made out of corn stalks. yworryfarm.net
