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First Sunday Arts Festival

West and Calvert Streets

Enjoy live entertainment and the works of 100 local and regional artists as you stroll along the first block of West and Calvert Streets next to Whitmore Parking Garage. Local restaurants set up outside cafes that are perfect for people watching and an afternoon bite to eat. Free parking for the family-friendly event is available at the state parking garage on the corner of Calvert and Bladen Streets.

London Town Summer Concert Series

Sunday, August 6 - Shenandoah Run Enjoy music in gardens overlooking the South River. Bring your family (and your dogs!) and spread out on our lawn for a relaxing time. Bring a picnic or visit a food truck! Drink purchases support London Town's programming. No alcohol is allowed to be brought on site but can be purchased at London Town. Rain or shine.​ Free with a suggested donation of $10 per person.

Family Program Series: Hearth & Home: The Colonial Herb Garden

Hammond-Harwood House 19 Maryland Ave, Annapolis, MD, United States

In this hands-on program participants will learn what herbs were cultivated in colonial Maryland and how they were used for cooking and medicine.  The program features a scavenger hunt, tour of the museum, and a craft. Program is 90 minutes long. $15 per family    

MTPA’s Artists in the Park

MTPA’s Stage One Park Place, Annapolis, MD, United States

August 9: Skribe (www.skribestudios.com/) In conjunction with Naptownmusic, MTPA is celebrating local performers and artists this summer with Artists in the Park. This FREE series offers families a chance to enjoy good music and good food in the great outdoors. Guests should bring a chair or blanket to enjoy the music!  

Dinner Under the Stars

Downtown Annapolis

The first block of West Street (from Church Circle to Calvert Street), located in the heart of the Arts District, will be closed to traffic on Wednesday evenings and filled with cafe tables reminiscent of the open-air cafes in France, Spain, and Italy. Visitors and area residents are invited to dine, stroll and shop along West Street while enjoying the live music beneath a canopy of lights above.

Wednesday Night Sailboat Races

Spa Creek Bridge Annapolis, MD, United States

Grab your favorite dockside seat in America’s Sailing Capital to watch some 130 crews compete in midweek races that involve sailing around several marks in the Chesapeake Bay before heading back to Spa Creek for a finish in front of the Annapolis Yacht Club. For many, the post-race party is the official beginning of the weekend. Best places to view the race include Annapolis City Dock and the Spa Creek Bridge First gun is approximately 6:10 p.m.

CBF Bridal Showcase

Philip Merrill Environmental Center 6 Herndon Avenue, Annapolis, MD, United States

Join the Chesapeake Bay Foundation for their Annual Bridal Showcase for a night of music, cocktails and hors d'oeuvres sampling, and raffle opportunities while taking in gorgeous views of the Bay! The Bridal Showcase will feature 25 wedding vendors and is free to attend!

Fine Wine and Finer Music with the Annapolis Chamber Music Festival

Hammond-Harwood House 19 Maryland Ave, Annapolis, MD, United States

In the elegant ballroom of the Hammond Harwood House, enjoy musical selections paired with wines curated by experts at Annapolis' Bin 201. Doors open at 6:30pm to allow guests to take a guided look at the historic house. The performance begins at 7:00 p.m. Tickets: $40 per person / $35 for members  

Tides and Tunes Concert Series

Annapolis Maritime Museum 723 Second Street , Annapolis, MD, United States

August 10 - Mike McHenry Tribe The Tides & Tunes Summer Concerts Series offers ten weeks of popular music from rock to folk to jazz with the incomparable backdrop of the Chesapeake Bay. Concerts are free; however, donations are requested. Food and spirits are available. The concerts are sponsored and supported by the popular Annapolis radio station WRNR.  

ArchiTrex Tours

Downtown Annapolis

Explore Annapolis – a Museum without Walls – on this new architecture tour that connects the city’s most notable homes and buildings to history. Join a professional architect on a two-hour walking tour. Learn about some of the most notable 17th and 18th century architecture in Annapolis. An unforgettable narrative and leisurely trek awaits. Highlights of the tour include Shiplap House, Patrick Creagh House, Maryland State House, Hammond-Harwood House and Chase-Lloyd House. Departs from Information Booth at City Dock Admission: $22/Adults, $14/Children 3-11, 2 and under free