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October Events in Dorchester County

October 1 @ 12:00 am - October 30 @ 12:00 am

Hurlock Fall Fest

NEW DATE! October 8 • 8 a.m.-5 p.m.

Train Station, Gay Street, and Main Street, Hurlock

The day kicks off with a parade down Main Street at 10 a.m. while craft vendors will be on site at the train station from 8 a.m. to 4 p.m. Round trip train rides from Hurlock to Federalsburg depart at 11 a.m., 12:30, 2, 3:30, and 5 p.m. Tickets may be purchased at the town office or call 410-943-4181. The Little Miss and Little Mister Fall Festival Contest begins at 12:30 p.m. at the train station. Motown and soul music will be performed by The Winstons from 11 a.m.-2 p.m. Other highlights include a petting zoo (10 a.m.-2 p.m.), pony cart rides and Zoo to You by the Salisbury Zoo. Food is available for purchase starting at 8 a.m.

Skipjack Sail

October 1, 8, 15, 22, 29 • 1-3 p.m.

Long Wharf, Cambridge

Join the Skipjack Nathan of Dorchester, an authentic traditional oyster dredging vessel and Maryland’s state boat, for a two-hour cruise on the Choptank River. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance reservations are recommended and accepted online until midnight of the day before the sail. The Nathan carries up to 20 passengers per trip. For details, visit www.skipjack-nathan.org.

Harvest Festival

October 2 • Noon-5 p.m.

Layton’s Chance Vineyard & Winery, 4225 New Bridge Road, Vienna

Enjoy food, grape stomping, hayrides, moon bounce, wine tasting, live music by Carley Twigg and Charlie & The Cool Tones, and more. Call 410-228-1205 for details.

Cambridge Farmers’ Market

October 6, 13, 20, 27 • 3-6 p.m.

Long Wharf, High and Water streets, Cambridge

Find local produce, meats, cheeses, crafts and more each Thursday through October. For more details, visit Facebook @CambFarmMarket.

Ghost Walk

October 8, 14, 22, 28, 29 • 7 p.m.

Spring Valley Park, Dorchester Courthouse, Spring and High streets, Cambridge

Take a walk down Haunted High Street, 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. The tour is suitable for adults and kids. Cost is $20-25. Visit chesapeakeghostwalk.com.

Spooktacular Second Saturday and Art Walk

October 8 • 4-8 p.m.

Downtown Cambridge

This monthly celebration in downtown Cambridge features an Art Walk with free art gallery receptions, as well as specials in the independently owned shops and great dining. Shops and galleries are open all day and into the evening. The Art Walk starts at 5 p.m. Live music is on tap at several restaurants later in the evening. As always on Second Saturday, downtown’s restaurants will be busy, so call ahead with your dining reservations. Plenty of free parking. Updated info at DowntownCambridge.org.

Second Saturday Book Sale

October 8 • 9 a.m.-1 p.m.

Dorchester County Library, 303 Gay Street, Cambridge

The Friends of the Library hold its Monthly Book Sale at the Cambridge location of the Dorchester County Library on the second Saturday of the month from 9 a.m. to 1 p.m. The sale offers a wide range of fiction, history, cooking, gardening, non-fiction and more at bargain prices. Call 410-228-7731.

Jazz at the Mural

October 8 • 6 p.m.

Cannery Way, 424 Race Street, Cambridge

Enjoy the sounds of Howie Jung in front of the “Take My Hand” mural. The trio is a force rooted in bebop, jazz, blues and gospel. They are also the recipients of the governor’s citation for 20 years in the performing arts. For tickets, visit harriettubmanmuseumandeducationalcenter.com.

Decoy Carving Class

October 8 • 10 a.m.-2 p.m.

Dorchester County Historical Society, Cambridge

Join master carver Zeke Willey for beginning as well as seasoned carvers and learn the Ron Rue-style dove decoy carving technique. Six classes will be held every other Saturday starting October 8. Call 410-228-7953 to reserve a spot.

Underground Railroad Bike Event

October 15 • 8 a.m.

Cambridge South-Dorchester High School, Cambridge

This unique bike ride (26 or 46 miles) will follow the part of the Underground Railroad through scenic marsh and farmlands, with rest stops at historic sites. Cyclists will experience Harriet Tubman’s journeys, while helping to raise funds for the statue. This ride is one of the many community efforts, coordinated by Alpha Genesis Community Development Corporation, to raise money and awareness of the county’s rich heritage. Bikers will leave from Cambridge South-Dorchester High School and travel along the same routes that Harriet would have traveled. Visit www.bikesignup.com/Race/MD/Cambridge/BikeTheUGRR to register.

Kite Festival

October 16 • Noon-4 p.m.

Sailwinds Park, 2 Rosehill Place, Cambridge

Bring the family to watch kites of all shapes and sizes. Bring a kite or simply wonder at the kites as they soar above the shores of the Choptank River. Call 410-228-1000 with questions.

Fun Dog Show

October 22 • 9 a.m.-1 p.m.

American Legion, 98 Sunburst Highway, Cambridge

This local tradition includes a raffle, a blessing of the animals, a parade of dogs at 10 a.m. and more. Registration begins at 9 a.m. A portion of proceeds benefits the Baywater Animal Shelter. Call 410-228-3161 with questions.

Guided Birding Tour

October 30 • 8 a.m.-Noon

Blackwater National Wildlife Refuge, 2145 Key Wallace Drive, Cambridge

Join a guided birding tour with veteran birder. Bring binoculars and field guides and dress for the weather. Meet at the visitor center and caravan via car to birding hotspots along Wildlife Drive. Call 410-228-2677 for more information.


October 1 @ 12:00 am
October 30 @ 12:00 am


Dorchester County
MD United States + Google Map
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Allison Rogers



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