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Memorial Day Weekend Activities

May 26, 2016 03:38PM ● By Cate Reynolds
Yes, having an extra day off work is always a cause for celebration. But let's not get caught up in the excitement of a long weekend and forget the real purpose of Memorial Day -- honoring those in the military who have sacrificed their own lives to protect our own. Here are some ways we can show our respect while taking the time to be thankful we are able to bring together our community to enjoy such events.

Annapolis Memorial Day Parade

May 30th, starting at 10 a.m.
The parade follows the traditional route on West Street, goes around Church Circle, down Main Street, and ends at City Dock. Marching bands, as well as veteran, community, and patriotic organizations will be part of the parade honoring and remembering those who have died serving our country. Immediately following the parade will be the annual wreath laying ceremony at Susan Campbell Park. This ceremony is open to the public and all are welcome.

Run to Remember Memorial Day 5K

Wicomico Youth & Civic Center, 500 Glen Ave, Salisbury, MD 21804, Saturday, May 28, 9 a.m., $20 – 30, 410-548-4900 x115,
Tie up those laces and head over to the Wicomico Youth & Civic Center for the Run to Remember Memorial Day 5k Run/Walk and honor our nation’s fallen heroes on Saturday, May 28th starting with check –in and registration at 8 a.m. Participants will begin at 9 a.m. on gravel paths and dirt trails through Salisbury City Park and end at the Wicomico War Veteran’s Memorial. Those who are looking to be extra competitive, awards will be presented to the top three male and female finishes in five age categories! Registration will continue through to race day and all ages/leashed pets are welcome to participate. Pre-race day prices are $25 per person and $20 military with ID (register in person only). Price day of the race will be $30 per person.

Chesapeake Beach Stars and Stripes Festival

Chesapeake Beach, MD 20732, Saturday, May 28th through Monday, May30th, (Saturday festivities start at 10 a.m., Sunday 11 a.m., Monday 10 a.m.), 410-257-2230, 
Join the town of Chesapeake as they honor our fallen heroes in the 5th annual Stars & Stripes three day Festival starting Saturday, May 28th. Opening Ceremony will begin at 10 a.m. at the Chesapeake Beach Veterans’ Memorial Park with music performed by the U.S. Naval Academy Band Brass Quintet. Sunday is family fun day at Kellam’s Field! Bring the family and enjoy a full day of activities, live music, stage performances, crafts and games, and living historians and demonstrations. Monday will conclude the weekend with an American Legion Memorial Day Ceremony at 10 a.m. and a moment of silence at 3 p.m.

Additional Events This Weekend

Annapolis Summer Garden Theatre Opening Season

May 26, 2016, 8:30PM
The Annapolis Summer Garden Theatre celebrates 50 years this season! Kicking off the season this month, they’re presenting The Wedding Singer (May 26th–June 18th). Rent opens June 30th and runs through July 23rd. And later in the season The Producers (August 4th–September 4th). Shows take place weekly from Thursday through Sunday at 8:30 p.m. (with some Wednesday shows) and tickets are $22 per show or $56 for the season. For more information call 410-268-9212 or visit

Paint Annapolis

May 30-Jun 05, 2016
Paint Annapolis is a five day juried plein air painting competition held Monday, May 30th–Monday, June 5th with an exhibition of artwork Sunday, June 5th–Sunday, June 12th. For fourteen years, Paint Annapolis has been a premier event, bringing people around the world and our city to share in the spirit of outdoor painting. Paint Annapolis features 30 juried artists from around the world for five days of competitive painting. Two painting events will be open to the public, a Nocturne, or night painting, on Tuesday, May 31st and Dueling Brushes, a quick draw competition, on Sunday, June 5th. For more information call 410-268-4566 or visit

Chestertown Tea Party

Friday, May 27th through the 29th, Times vary
The Chestertown Tea Party Festival celebrates colonial resistance to British rule with historical happenings during the weekend of Friday, May 27th through the 29th. In response to British Parliament’s closing of the port of Boston, the citizens of Chestertown, Maryland met in May of 1774 and set forth “Resolves” forbidding importing, selling, or consuming tea in Chestertown. According to local legend, residents then gathered at the town center, marched down High Street to the brigantine Geddes, which was anchored in the Chester River, and tossed her cargo of tea overboard. The annual reenactment is the centerpiece of the Chestertown Tea Party Festival and takes place at 2 p.m. on Saturday. All Festival events take place along the Chester River and in the historic district of 18th-century Chestertown. Festivities include: the Colonial Parade, Street Party, Raft Race, street performances, colonial crafts, musicians, a 5K and 10K mile run, and more. The Wine and Craft Beer Tasting is Sunday at Wilmer Park noon–4 p.m. featuring local Maryland wineries and brewers. For more information visit

Cambridge Classic Powerboat Regatta

May 28, 2016, 1:00PM
The oldest powerboat in the United States, historically known as the Cambridge Classic Powerboat Regatta, returns for its 106th running in Cambridge on Memorial Day weekend, May 28-29, with a pre-race concert on May 27th. Twelve classes of boats featuring hydroplanes, runabouts and Jersey speed skiffs will race each afternoon from 12pm–5pm (weather permitting) on the Choptank River off Great Marsh Park, 1 Somerset Ave. in Cambridge, MD. Spectators can tour the pit area beginning at 10am. Admission is free with a $5 a day charge for in/out parking. Food and drink will available.

24th Annual Soft Shell Spring Fair

May 29, 2016, 12:00PM
The 24th Annual Soft Shell Spring Fair is Sunday, May 29th noon–5 p.m. Taking place at Crisfield City Dock, this delicious event features soft crabs and seafood of all kinds, kids’ activities, arts and crafts, demonstrations, entertainment, and more. For more information call 410-968-2500 or visit

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