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What's Up Magazine

Our List of Can't-Miss Events from the Region

Jul 21, 2014 03:01PM ● By Cate Reynolds


Chincoteague Wild Pony Swim
Each year, approximately 40,000 visitors come to check out the Chincoteague Wild Pony Swim at Chincoteague Island. The swim will be held Wednesday, July 30th, with the time announced the day prior to the event due to tidal conditions. Around 150 ponies make the swim across Assateague Channel, a historic passage that has taken place since 1924, and afterwards, the annual carnival is held in celebration. For more information, visit
—Kylie Taylor

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Pirates and Wenches Fantasy Weekend
Drink up, me hearties! The Pirates & Wenches Fantasy Weekend takes place Friday, August 8th through Sunday, August 10th in Rock Hall. From a decorated dinghy contest and sea shanty sing-a-long to rum tastings and the Buccaneer’s Ball, there’s plenty o’ ruckus to be had, including children’s activities for the lil’ swashbucklers! General admission is free. More information at

St. Mary’s College Governor’s Cup Yacht Race
The oldest and longest overnight race held on the Chesapeake Bay, the Governor’s Cup Yacht Race is set to take place Friday, August 1st and Saturday, August 2nd. The race runs from Maryland’s capital city to its first capital in St. Mary’s City. Vendors and a dinner will be provided at the Campus Center. To find out more about the race, visit
—Kylie Taylor

Maryland Renaissance Festival
Head back in time at the Maryland Renaissance Festival, where jousting, turkey legs, and artisans abound. The festival starts August 23rd, and runs through October 19th, on Crownsville Road in Anne Arundel County. For ticket pricing and details, visit
—Kylie Taylor

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Monty Alexander Jazz Festival
Head over to Easton for the Monty Alexander Jazz Festival, where big names such as Frank Vignola will be playing. Vignola is the guitarist of choice for some of today’s biggest musicians, such as Madonna and Ringo Starr. The event runs from August 28th through the 31st. For information on ticket pricing, visit
—Kylie Taylor

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Silopanna Music Festival
The Flaming Lips headline this year’s festival named after the state’s capital where it was launched in 2011 (it’s Annapolis spelled backwards!). The action begins at 11 a.m. Saturday, August 16th at the Anne Arundel County Fairgrounds in Crownsville. In addition to the Grammy-winning headliner, more than 15 musical guests are slated for the day-long event, including Dashboard Confessional, Matt & Kim, and Hellogoodbye. General admission tickets are $59.50, although that price increases to $69.50 after August 1st. A limited amount of VIP tickets are available. For more information, visit

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The 12-Ounce Regatta
Calling all MacGyver fans! The 12-Ounce Regatta challenges contestants with creating a model sailboat out of a few core materials: a hanger, some tape, and a six-pack. The hand-crafted vessels compete in races throughout the day in this annual fundraiser, hosted by the Chesapeake Outdoor Group. The event runs from 9:30 a.m. to 7 p.m. on Saturday, August 16th, at the Eastport Democratic Club in Annapolis. Live music, food, drinks, a silent auction, and other activities throughout the day. More information at

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“Kegs and Corks” – The Craft Beer and Maryland Wine Festival
Finally a festival both beer and wine lovers can enjoy together! Kegs and Corks, the Third Annual Craft Beer and Maryland Wine Festival, will be held Saturday, August 23rd from noon to 6 p.m. at the Anne Arundel County Fairgrounds in Crownsville. Benefitting the Chesapeake Bay Trust, the event boasts dozens of breweries and wineries, along with live music, delicious food, and local artisans. Tickets are $30 in advance; $35 at the door. Designated drivers get in for $10; tickets for ages 13 to 20 are $10; and children 12 and under are free with a paying adult. More information at


Choptank Heritage Skipjack Race
The Choptank Heritage Skipjack Race is a race for bragging rights, not prizes. Nine or 10 boats race each year in an effort not only to gain pride, but to keep the heritage alive. This year’s race is set for Saturday, September 27th in Cambridge. The start and finish of the race are best seen from Long Wharf, where seating and food will be available. For more information, visit
—Kylie Taylor

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Chesapeake Film Festival
From laugh-out-loud comedies to eye-opening documentaries, the Chesapeake Film Festival offers a plethora of independent, award-winning, and foreign films during its seventh year. Screenings will be held at various times throughout the weekend of September 19th at several locations in Easton. The event kicks off with an opening night party on Friday and ends with a closing night reception on Sunday. Tickets are $10 per screening with VIP festival passes offered for all access. More information at

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Summer Sendoff: Blues, Brews, and BBQ
The perfect closing to summer, the Summer Sendoff on Saturday, September 13th, takes over the 400-blocks of Poplar and Race streets in Cambridge, where food by local chefs and performances by area musicians serve as entertainment. The Wacky Main Street Mile Relay Race is also set to occur, but it’s no ordinary relay, with an egg walk and cycling on a kid-size tricycle as some of the challenges. Admission is free, but donations appreciated to support Cambridge Main Street. For updated information, visit
—Kylie Taylor

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Run for Shelter
Even the most novice runner can partake in the Run for Shelter race, which offers a two-mile walk, 5K and 10K races, a half marathon, and even a kid’s fun run! The event, which benefits Haven Ministries, will be held on Saturday, September 13th, with registration at 6:30 a.m. at Kent Island High School in Stevensville. Prices vary depending on race. More information at

Maryland Seafood Festival
Crab cakes, steamed shrimp, oysters on the half shell, lobster rolls, and so much more, the Maryland Seafood Festival returns to Annapolis on September 6th and 7th. Along with live entertainment, regional arts and crafts vendors, chef demonstrations, and wine and beer tastings, it’s an event not to miss. Held at Sandy Point State Park, the festival runs from 10 a.m. to 9 p.m. Saturday and 10 a.m. to 7 p.m. Sunday. General admission tickets are $15, with VIP tickets available. Children 12 and under are free. For more information, visit

Taste of the Sassafras
The Taste of the Sassafras is coming again for its fourth year in Galena. Tickets go on sale in August, with the event taking place Friday, September 12th. Some of the vendors from last year’s festival were The Granary, Kitty Knight House, and Sassafras River Beef. For more information, visit
—Kylie Taylor

Annapolis Craft Beer and Music Festival
The Annapolis Craft Beer and Music Festival brings together the perfect pairing of microbrews and live music from noon to 6 p.m. Saturday, September 13th, at the Navy-Marine Corps Memorial Stadium in Annapolis. General admission tickets are $40 with unlimited tastings of more than 100 craft brews. Tickets are $20 for designated drivers; $10 for ages 13 to 20; and free for those under 12. Don’t forget to bring a chair! More information at


Bark in the Park
Celebrate man’s best friend on Saturday, October 18th during the Fifth Annual Bark in the Park. Benefiting Talbot Humane, the event kicks off at 9 a.m. with a 5K fun run and dog walk, followed by a dog show, vendors, food, and music at Idlewild Park in Easton. New this year, the event will compete for the Guinness World Record title of most costumed dogs in one place (the number to beat is 337!). General admission is free. More information at

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Nanticoke River Jamboree
The Fourth Annual Nanticoke River Jamboree will be held Saturday, October 11th at Handsell in Vienna, with a suggested donation of $4 per person or $10 per family. Presented by the Nanticoke Historic Preservation Alliance, the event runs from 10 a.m. to 5 p.m., with re-enactors, music, exhibits, food, and crafts. For more information, visit

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Taste of Kent Narrows
The family-friendly Taste of Kent Narrows offers tastings from the area’s finest restaurants and live entertainment on Saturday, October 11th at the Chesapeake Heritage & Visitor’s Center in Chester. Tastings run from noon to 4 p.m., with the entertainment continuing until 5 p.m. Tickets are $30 in advance; $35 at the door; children eight and under are free with paying adult. More information at

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Oyster Festival
Fried, stewed, and freshly-shucked oysters abound at the 16th Annual Oyster Festival at the Captain Avery Museum in Shady Side. The festival, which benefits museum programs, runs from 12:30 to 5 p.m. on Sunday, October 19th. Admission is $6 per adult; $2 for children under 12. There is a modest fee for food and beverages. For more information, visit

United States Naval Academy Halloween/All Saints Concert
Enjoy an evening of music, light, drama, and dance on Friday, October 31st and Saturday, November 1st, at the United States Naval Academy’s annual Halloween concert. A wide selection of music from various genres will be performed by Monte Maxwell, Chapel organist, and other midshipmen. Show starts at 8 p.m. both nights. More information at

The 2014 U.S. Sailboat and Powerboat shows
The nation’s oldest and largest in-water boat show, the United States Sailboat Show, returns October 9th through 13th at City Dock in Annapolis. Now in its 45th year, the event offers the largest multi-hull collection in the world. The following week brings the United States Powerboat Show back to Annapolis. From October 16th through the 19th, boating enthusiasts can peruse everything from luxurious motor yachts to offshore fishing machines at City Dock. For both events, two-day admission tickets are $31; one-day admission tickets are $18; children’s tickets are $5; and those six and younger are free. VIP tickets and boating excursions available. For more information, visit

Patuxent Wildlife Festival
The Patuxent Wildlife Festival brings together live animals, children’s crafts, tram tours, scientific demonstrations, and behind-the-scenes research tours of the Patuxent Wildlife Research Center in Laurel. The event, which runs from 10 a.m. to 3 p.m. Saturday, October 18th, is free, although there is a $3 charge for tram tours. More information at

Rock Hall FallFest
It’s a celebration of family, community, and oysters at the 17th Annual Rock Hall FallFest on Saturday, October 11th. Enjoy live music on two stages, 50 craft booths, lots of food, and activities for the youngsters from 10 a.m. to 4 p.m. on Main Street in Rock Hall. General admission is free. For more information, visit


Belgian Beer Festival
Twenty dollars goes far at the Belgian Beer Festival on Saturday, November 8th in downtown Cambridge. For a single Jackson, you get a tasting glass and as much beer as you can fill it with! Dozens of beers from Belgium and locally inspired Belgian brews will be served, along with live music provided by local musicians and food prepared by nearby eateries. More information at

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Annapolis by Candlelight
Take a stroll through several private homes along King George, Prince George, Maryland Avenue, and East streets during Annapolis by Candlelight on Friday, November 7th and Saturday, November 8th. Presented by Historic Annapolis, the walking tour, which runs from 5 to 9 p.m. both days, showcases some of the city’s finest architecture. Tickets are $30 for general admission and $25 for HA members and volunteers, with the price increasing to $35 after November 2nd. More information at

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Waterfowl Festival
Celebrate the Eastern Shore in all its waterfowl glory at the annual Waterfowl Festival to be held November 14th through 16th in Easton. Artists, exhibitors, demonstrations, kid’s activities, and more, with the 44th Annual Premiere Night Party on Thursday, November 13th to benefit Waterfowl Chesapeake Inc. Festival tickets are $15, and children under 12 are free. Tickets for the Premiere Night start at $125, and include festival admission. More information at

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Maritime Republic of Eastport’s Tug of War
The City of Annapolis and the Maritime Republic of Eastport will duke it out once again during the 17th Annual Tug of War to be held Saturday, November 8th. Each team stands on its respective side of Spa Creek for seven “tugs,” competing for the championship title (Eastport was victorious last year!). The annual “Slaughter across the Water” begins at noon and benefits various local charities. More information at


Eastport Yacht Club Lights Parade
A dazzling spectacle of illuminated boats along Spa Creek, the Eastport Yacht Club Lights Parade occurs every year on the second Saturday in December. This year, the parade runs on Saturday, December 14th from 6 to 8 p.m. Whether you partake as a participant or a spectator, it’s the perfect way to celebrate the holiday season. More information at

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Christmas in St. Michaels
Celebrate all things Christmas throughout the weekend of December 12th in the historic Eastern Shore town of St. Michaels. Festivities include breakfast with Santa, a gingerbread house competition, the Talbot Street Parade, holiday music, home tours, and more. Visit for more information.

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Annapolis New Year’s Eve Celebration
Ring in the New Year at City Dock in Annapolis during this free, family-friendly New Year’s Eve party. Entertainment kicks off at 3 p.m., with two fireworks displays at 7:30 p.m. and midnight. Face painting, magic shows, live music, and more! Visit for more information.

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Santa Swim
Brave the frigid temperatures and icy waters of the Choptank River for charity during the Santa Swim on Saturday, December 13th. In place of an entrance fee, swimmers raise funds to donate to the Care and Share Fund, Inc., which helps the needy in Dorchester County. The swim begins at 10 a.m., with treats and giveaways to follow. More information at