It’s October in Dorchester County — time to embrace all the season has to offer! — and to get out on the water before the weather gets too cold! Here are our top suggestions….

Pumpkins and Corn Mazes!

Nothing looks more like fall than those lovely orange orbs. Delight in U-Pick pumpkins and pumpkins of all sizes and shapes at Emily’s Produce or Breckenridge Adventures. Emily’s also has a free Milo and Corn Maze open daily while Breckenridge has a nine-acre Corn Maze open on Fridays (including Flashlight Maze after dark), Saturdays and Sundays.

Ghost Walk

Join in the Cambridge Ghost Walk led by Chesapeake Ghosts. The walk leads you along what’s known as the most haunted street in Maryland! October 13, 26, and 31.

Vampire Drama

The brand-new Groove Theatre Company’s first production is “Let the Right One In,” an eerie vampire story. October 11-13 and 19-21.


The wild oyster harvest season opened on October 1, which means you’ll see everything from oysters on the half shell to oyster stew in our restaurants. Many menus also feature oysters farmed right here in Dorchester. Get your fill of all kinds of oysters — and other mollusks like conch, periwinkle, and octopus — at the Hot Sauce and Mollusk Fest Oct. 14. Or immerse yourself in the oyster world by joining an Oyster Farm Tour and Tasting hosted by the new heritage tour company Matchcoat Sojourner, along with Snifters Craft Beer & Wine Bistro and Madhouse Oysters.
BONUS: It’s not just about oysters… it’s  still crab season, and this is the time of year when crabs are the biggest!

Halloween Fun for Adults

Who says only kids get to have fun at Halloween? Head to Layton’s Chance for Wine and Halloween Candy Pairing Oct. 27-28, or to RAR Brewing on Oct. 27 for their Halloween Party. Or join the Wine Bar for a Bloody Mary bar and showing of the classic scary movie “Halloween” on Oct. 7.

Halloween Fun for Kids

Cabin Fever Play Centre has their Halloween Bash on Oct. 28. Watch for various organizations hosting trunk or treat or other Halloween parties. And the official trick-or-treat time for the City of Cambridge is on October 31 from 6o to 8pm for ages 12 and under.


The classic German Oktoberfest is a fall tradition. Join in Crabtoberfest on Oct. 6 for an Eastern Shore twist on Oktoberfest.

Celebrate the Fall Harvest

You’ll find fall vegetables and fruits during the season’s last few weeks of the Cambridge Farmers Market. Check out the Beckwith Apple Festival on Oct. 20 in the Neck District with apples, apple treats of all kinds, a flea market, and more. Or get in the spirit of the grape harvest during Layton’s Chance Winery’s Harvest Festival, where you can try your feet at grape stomping or join a hayride.

Get Out on the Water

If you don’t have your own boat or kayak, be sure to join in one of the last sails of the season with the Skipjack Nathan of Dorchester or a cruise with Choptank Riverboats. Join Over Board Paddle & Fitness for a sunset stand-up-paddleboarding experience, or rent a kayak or SUP through Blackwater Adventures. Plus there’s great fishing — contact Sawyer Charters or Gootee’s Marine or Stoney Cover Charters for a day of angling.

Go Birding

Fall is a major time for birds and waterfowl to head to their winter spots. Since Blackwater National Wildlife Refuge is located along the Atlantic Fly-way, there are many opportunities to see the thousands of winged creatures moving through or stopping by for some food and rest. Bring the binoculars and go for a slow drive along the refuge’s Wildlife Drive, or join a free guided birding expedition on Oct. 28, Nov. 25, or Dec. 2.

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