Local Events

Cambridge Farmers Market on the waterfront at Long Wharf (near High and Water Streets) in Cambridge. Local produce, meats, cheeses, breads, crafts, and more. Every Thursday, 3-6pm, May through October.

Skipjack Cruises http://skipjack-nathan.org/ Have regularly scheduled public sails which depart from Long Wharf, at the end of High Street, in Cambridge, Maryland. Saturday Public Sails are two hours long and generally include an oyster dredging demonstration, conditions permitting. Each sail is unique, depending on wind, weather, captain and crew. They offer an unforgettable opportunity to experience sailing on a traditional Chesapeake Bay skipjack. All ages are welcome. Children 12 and under must be accompanied by an adult and must wear life jackets, which we will provide. No pets are allowed except service dogs. We can accommodate passengers in wheelchairs, but please let us know that on the registration form, as we can only take a limited number of wheelchairs each trip. Adult Cost $30 per person

Historic Walking Tours Join a costumed guide for a walking tour of beautiful, historic High Street. Every Saturday at 11am, from April through October. Weather permitting. Meet at Long Wharf at the end of High Street. $8 for adults; 12 and under free. Reserve at 410.901.1000.

Lighthouse Tours Take a free, self-guided tour of the Choptank River Lighthouse. Open daily, 9am-6pm in season (May through October) and by appointment (November through April; call 410-463-2653). Located at Long Wharf Park, near High and Water Streets in Cambridge. Find out more at choptankriverlighthouse.org.

Second Saturday and Art Walk
Shops and galleries stay open until at least 8pm with specials, free nibbles, and more. Every Second Saturday of the month, 5-9pm, on the 300 block of High Street, 500 block of Poplar Street, and 400 block of Race Street.

  September Events

VINEYARD DASH 5K
September 10 @ 10:00 a.m. at Layton’s Chance *Admission fee required
The Vineyard Dash 5k is a scenic trail-run through the vineyards at Layton’s Chance.  Immediately after the race is the 7th Annual Harvest Festival featuring agricultural arts and crafts, grape stomping, live music and much more.  Oh yeah, there will be plenty of wine to taste and purchase… AFTER the race! Register here today!

7TH ANNUAL HARVEST FESTIVAL
September 10 @ 11:00 a.m. at Layton’s Chance. *Admission fee required
It will be a day long celebration of the end of our Harvest season! There are plenty things to do for the adults and kids a like. Food and craft vendors, hayrides, pony rides, agricultural demonstrations, grape stomping, moon bounce, archery and goose call demonstrations, and so much more!

HARVEST FESTIVAL KIDS PAINT EVENT
September 10 @ 12:00 p.m.- 2:00 p.m. Price – $20/child
Layton’s Chance. This paint event occurs during our annual Harvest Festival. Join us for a full day of fun for the whole family! Painting – Sunny Scarecrow  (11×14 canvas size)

HARVEST FESTIVAL ADULT PAINT EVENT
September 10, 3:00 p.m. – 5:00 p.m.  at Layton’s Chance
Painting – Vineyard Vines  (11×14 canvas size). This paint event occurs during our annual Harvest Festival and includes free access. Join us for a full day of fun for the whole family! Price – $30/person (includes free access to festival)

SUMMER SENDOFF
September 10 @ 5:00 p.m. – 10:00 p.m.
Cambridge Main Street, Cambridge, MD. Help us say goodbye to another busy Summer season with this annual celebration of great food and music. We’ve got a few ideas for some changes to this awesome time, so stay tuned and we’ll make sure we update as soon as things become official.

BINGOMANIA
September 10
500 Glen Ave., Salisbury, MD. Bingomania, the Eastern Shore’s largest bingo cash prize event, returns to the Wicomico Youth & Civic Center. Doors open at 5 pm; regular games begin at 7:30 pm. You must be 18+. Admission $55.00 at the door, $45.00 in advance

DELMARVA BIKE FEST
September 15-18
31640 Winterplace Parkway, Salisbury, MD. The Annual Delmarva Bike Week presented by Rommel Harley-Davidson returns to Maryland’s Eastern Shore.

SUNFEST Ocean City 2016
September 22 –25
Inlet Parking Lot, Ocean City, MD. This nationally recognized festival brings family fun-filled days: music, food, arts & crafts. Nationally known & regionally popular entertainers perform four days. Entertainment is free except headline acts.

FIDDLERS CONVENTION
September 23– 25
Downtown Main Street, Berlin, MD. Blue grass and fiddlers grace the streets, competitions, food, beer garden, vendors

BEST FEST
September 24 @ 12 p.m.-9 p.m.
Olde Trappe Park, Trappe, MD. Youth festival created by kids, for kids! Games, vendors, talent showcase, electronic dance party. Helping every kid do their BEST!

CHOPTANK HERITAGE SKIPJACK RACE
September 24 @ 10:00 a.m.-12:00 p.m. Long Wharf Park, Cambridge, MD. One of only two skipjack races left on the Chesapeake Bay. The race takes place, 10am-noon, on the Choptank River off Cambridge, with the starting and finish lines near the entrance to Cambridge Creek. The best vantage points for viewing are at Long Wharf or Great Marsh Park, or on the water by boat. At Long Wharf there will be bleachers, food vendors, and a radio-controlled skipjack demonstration for those who like their skipjacks on a smaller scale. Cannons on…

CRABTOBERFEST
September 24 @ 4:00 p.m – 10:00 p.m.
Downtown Cambridge, MD. Dancing, music, German beer, German and American food are all part of Crabtoberfest. Eastern Shore and German fare including bratwurst, wienerschnitzel, red cabbage, steamed crabs, crab cakes, crab soup, knockwurst, sauerkraut, and crab pretzels. Also featuring carnival games and activities for kids of all ages.

DORCHESTER SHOWCASE
September 25 @ 10:00 a.m.- 2:00 p.m.
Dorchester Center for the Arts, 321 High Street Cambridge, MD. This annual event has become a tradition and celebrates its 40th year in 2016. Enjoy arts and crafts from local artisans as they line High Street from Dorchester Center for the Arts to Long Wharf.

October Events

HURLOCK FALL FESTIVAL
October 1, 2016 10 a.m.-5 p.m. Parade, Train Ride, Music, Food and Craft Vendors, carnival

POKEMOKETOBERFEST
Oct. 1, 2016 12:00 p.m.-8:00 p.m.6 Market St, Pocomoke City, MD
Beer and wine festival featuring many local breweries and wineries with lots of live entertainment.

IRONMAN MARYLAND TRIATHLON
October 1 Cambridge, MD
Join us downtown as we welcome back IRONMAN Maryland participants from around the world. Cambridge is the host of one of only 13 full-distance IRONMAN endurance races in North America, and we are one of the only two cities that hosts more than one IRONMAN event. There will be THOUSANDS of visitors in Cambridge that week, and downtown is buzzing with live music and entertainment every night.

WINE AND UNWIND
October 2, 1:00 p.m. – 4:00 p.m.  at Layton’s Chance
Come have a lazy afternoon with us!  Sip wine and enjoy live acoustic music by Justin Ryan.

DRESS FOR LIFE FASHION SHOW OF SURVIVORS
October 2, 5:30 p.m.- 9:30p.m. Show will start at 6:30pm  at Layton’s Chance
Join us for the First Fashion Show of Survivors, you will enjoy an evening filled with wine tasting, hors d’oeuvres, door prize raffles, shopping experience and the HIGHLIGHT of the event will be the Fashion Show of Survivors, we will have Survivors from Dorchester County walking the stage and strutting their stuff!!! You will not want to miss out on this event!  Feel Free to bring your lawn chair/blanket and spread out on the grass!  Tickets are $25 and must be purchased in ADVANCE.

ALL PROCEEDS GO TO DORCHESTER COUNTY RELAY FOR LIFE TEAMS!

TOAST & TOASTED
October 8, 5:30 p.m.- 8:30 p.m.  at Layton’s Chance
S’mores and wine pairing with live music, a food truck and a bonfire.  $7/person 21+ with advance ticket sales. $10/person 21+ at the door. Gold Leaf members are FREE

GOOD BEER FESTIVAL
October 8 – 9, 12:30 p.m.-6:30 p.m.  at Layton’s Chance
5561 Plantation Lane, Salisbury, MD. Features more than 80 craft beers, a Local Beer Garden, Beer Talks, Home Brew Competition, music, games and more. Tasting tickets: $25-40; non-tasting: $5-10.

  November Events

KARAOKE HAPPY HOUR
November 4, 6:00 – 10:00PM  at Layton’s Chance
Karaoke Happy Hour! Join us for singing, dancing, and all around good times! Bring your dinner and snacks to complete the night. Wine available at the bar! Table reservations taken on the day of the event only!

One Response to “Upcoming Local Activities in Dorchester County or Surrounding areas”

  1. Bryan and Jena

    Could not have had a better time or nicer hosts. Felt right at home and made us feel welcome as soon as we arrived. You have a beautiful home and yard and just a perfect setting for a B &B. Great food, wine and new friends. What more could you ask for

    Reply

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