Updated November 1, 2023

Fall is in the air! Below are a few ways to embrace the season in Dorchester County on Maryland’s Eastern Shore with seasonal fun for all ages!  It’s also a great time of year for cycling, birding, fishing, boating, and the last few weeks of paddling before the winter chill sets in. We have free guides for cycling, birding, and paddling in Dorchester County. And you’ll find more resources for outdoor adventure here.

Emily's Produce - fall pumpkins - Cambridge, MD - Photo by Jill Jasuta

Pumpkins galore at Emily’s Produce in Cambridge. Photo by Jill Jasuta


Pick Your Own Pumpkins

Choose from lots of pumpkins and gourds while wandering through the pumpkin patch at Emily’s Produce, or pick from the crates filled with different sizes and types.

Cambridge Ghost Walk - Photo courtesy Chesapeake Ghosts

Cambridge Ghost Walk
Nov. 3, 11, 17, 25

Take a guided walk down Haunted High Street in Cambridge – the most haunted street in Maryland! Hear about the ghosts who haunt and strange events that have happened in just a few short blocks. Soldiers, Governors, jilted women, Oystermen, an eccentric cat lady, a dying daughter, slain war heroes, suicidal bankers, murderous merchants, laughing children and a one-legged sea captain are some of the spirits that hang around High Street. Reserve ahead.

Toast & Toasted
Nov. 3, 6:30-9:30pm

Layton’s Chance Winery hosts a fall evening with 4 unique s’more combinations paired with four different wines for 21 and over. Live music from Double Nickels. Roast marshmallows over the fire pits. Bring a chair & blanket if it’s chilly! $20/person, 21+ only. Food trucks will NOT be provided; bring your own snacks and dinner. Tickets.

Halloween Party & Costume Contest – Johnny’s Tavern
Nov. 4, 9pm

Keep the Halloween spirit going! Johnny’s Tavern in East New Market has a Halloween Party & Costume Contest with drink specials, costume contest, music by DJ Alchemist. This party is usually standing-room only, so get there early! $10 cover

Corn Maze - Emily's Produce, Cambridge, MD - Photo courtesy Emily's ProduceSunset in the Stalks
Nov. 10, 5-8pm

Emily’s Produce stays open late for some family-friendly fun! The Corn Maze will be open for flashlight explorers (bring your own flashlight). Music, after-hours shopping, fall cocktails and beer, s’mores roasting.

Fall Crafting at Phippin’s Crafting Corner
Throughout the season

Phippin’s Crafting Corner in Cambridge has a range of fall and crafting sessions for all ages, including fall wreaths and centerpieces and more.


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