Executive Inn & Suites, Leonardtown MD.  
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History of Leonardtown
Call: 301.475.3000 | Fax: 301.475.3002


In Leonardtown:

First Fridays:
5 pm- 8 pm on the first Friday evening of every month year round. Stroll the sidewalks of downtown Leonardtown. Many retailers offer something special for First Friday, including live music, poetry readings, book signings, cooking classes, and jewelry making. Browse the galleries and meet the artists then complete the evening with dinner at one of the town’s restaurants where you may find dinner and drink specials. For more information, visit www.leaonardtownfirstfirdays.com

Downtown Tunes:
Beginning at 6 pm on the fourth Saturday in May, June, July and August.
Leonardtown square is the scene is the scene for this series, which features a variety of music genres such as acoustic music, country/bluegrass and rock and roll. Concert goers are invited to bring charis or blankets and sit on the green. Music may also be enjoyed by diners at the outdoor tables of some of the restaurants situated around the square.

Leonardtown Annual Events:
For exact dates and more information, call 301.475.9791 or visit www.somd.com/leaonardtown or www.visitstmarysmd.com


Earth Day Celebration:
3rd Sunday in April. Leonardtown Square. 12:30pm-4:30pm. Live music, entertainment, environmental demonstrations, recycling information, plant sale and other activities.

Spring Fling Car Show:
4th Sunday in April. Leonardtown Square. 8am-4pm. Classic and antique cars and live entertainment.


Beach Party on the Square:
1st Saturday of August. Leonardtown Square. 4pm-9pm. Family entertainment, music, sand volleyball, jump rope and hula-hoop contests, games, prizes, and crafts.


Fall Follies on the Square:
2nd Saturday in September. Leonardtown Square. 10am-3pm. Arts and crafts festival, paintings, wood carvings, stained glass, ceramics and jewelry.

Leonardtown Wharf Waterfront Celebration:
2nd Saturday in September. Leonardtown Wharf. Noon-5pm. Sailboat races, water-related exhibits, kayak and canoe guided tours, food and entertainment.

Taste of St. Mary’s:
Held in September. Leonardtown Square. 12noon-5pm. Sample menu items of some of St. Mary’s County’s finest restaurants.


Scarecrow Making and Trick-or-Treating on the Square:
Week before Halloween. Leonardtown Square. 1pm-3pm. Scarecrow-making. 3pm-4pm. Trick-or-treating with downtown merchants.


Veterans Day Parade & Memorial:
November 11. Washington Street. 10 am. Marching bands, military units, Native-American dancers, horses and classic cars. Memorial ceremony and wreath-laying.

Christmas on the Square & Annual Tree Lighting:
4th Friday in November. Leonardtown Square. 5pm-9pm. Holiday festivities, music, entertainment, sleigh rides, horse & carriage rides, live nativity, tree lighting and Santa’s arrival.


Santa & Mrs. Claus on the Square:
2nd Saturday in December. Leonardtown Square. 11am-1pm.


Events around the County:

Fairs & Festivals:

Maryland Day:
-March 25. St. Clement’s Island Museum. Celebrate Maryland’s Birthday at the site of the first colonial landing in 1634.

Maryland Day:
-4th Sunday in March. Historic St. Mary’s City.

The Garden Fair at Sotterley Plantation:
-3rd weekend in April. Sotterley Plantation.

St. Clements Island History & Heritage Day:
-2nd Saturday in June. St. Clement’s Island.

Wine in the Garden:
-2nd Saturday in June. Summerseat Farm.

St. Mary’s Crab Festival:
-2nd Sunday in June. St. Mary’s County Fairgrounds, Leonardtown. 11am-5pm

An Independence Day Concert Celebration at Sotterley:
-July 4th. Sotterley Plantation. 1pm-4pm.

Potomac Jazz & Seafood Festival:
-2nd Saturday in July. St. Clements Island Museum, Coltons Point

St. Mary’s County Fair:
-3rd week after Labor Day. St. Mary’s County Fairgrounds. www.smcfair.som.com

-4th Saturday in September. Historic St. Mary’s City. 10am-5pm

Blessing of the Fleet:
-1st weekend in October. St. Clement’s Island. 10am-10pm

Riverside WineFest at Sotterley:
-1st weekend in October. Sotterley Plantation. 12pm-6pm www.sotterley.org

Ghosts of Sotterley Tours:
-3rd week in October. Sotterley Plantation. 7pm-10:30pm

Oyster Festival:
-3rd weekend in October. St Mary’s County Fairgrounds, Leonardtown. www.usoysterfest.com
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