Event Picks for July 2024

A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of July. Event dates may be subject to change.

Fourth of July Weekend in Annapolis

Annapolis is continuing the tradition of making downtown the destination of Fourth of July weekend. Start off with Dinner Under the Stars on West Street on Wednesday July 3rd. Enjoy an evening with family and friends under a canopy of white lights while enjoying live music and art demonstrations just ahead of the City’s July 4th festivities. On the big day, gather downtown in the city to salute our nation with marching bands, old and new fire engines, cars and vans, service clubs and scouts for the July 4th Parade. The parade will kick off at 6:15 p.m. at Amos Garrett and West Streets. The route will head down West Street, around Church Circle and down Main Street. Annapolis will then launch fireworks from a barge in the Annapolis Harbor at 9:15 p.m. Set up in public spaces northeast of the Severn River, City Dock, and along the Naval Academy Bridge, any of the street end parks facing Spa Creek, or aboard a boat in the Annapolis Harbor for the best views. The weekend will end on Sunday with the First Sunday Arts Festival on West Street with over 100 art and craft vendors, cafe dining, and live entertainment. Find more information on these events at visitannapolis.org.

Whispering Winds Pow Wow

Pow-Wow, an American Indian owned and operated organization, is sponsoring the 30th Annual Howard County Whispering Winds Pow-Wow/American Indian Show and Festival at the Howard County Fairgrounds in West Friendship on July 13th and 14th. This festival is an opportunity for the public to interact with American Indian dancers, singers, drummers, artists, and crafts persons. This event is also to educate about American Indians, past and present, through the arts. The event will kick off with a parade of nations at noon on Saturday and Native American food items will be for sale: Indian fry bread, Buffalo stew, Indian tacos, Indian corn soup, and more. For more information, visit howardcountyfairmd.com.

Bay Paddle 

The 2024 Bay Paddle takes place on July 20th at Kent Island Yacht Club and is co-hosted by Kent Island Outrigger Canoe Club. There are three races: a 3-miler, 10-miler, and a 35-mile circumnavigation of Kent Island. All registration fees for the race are donated to Oyster Recovery Partnership, Chesapeake Conservancy, and Waterkeepers Chesapeake to help protect the Bay. The post paddle party is a traditional luau sponsored by Tito’s and Pacifico and open to all from 3 to 5 p.m. More details are online at baypaddle.org.

Speak Your Truth

The Annual Speak Your Truth event is back on July 13th at ArtFarms Studios in Annapolis with the mission to stop the stigma of mental illness through a day of art & expression. Speakers at the event will include various types of expression, from song and poetry to comedy and dance--there will five-minute open mic times for those who want to share. The listeners of the event are just as important. Listeners will help everyone feel connected, get educated, and be inspired to take action, remembering that not everyone’s truth is the same. Speak Your Truth has worked since 2017 to talk about mental health in a way that is entertaining and engaging. In the past, visual and vocal artists, dancers, clothing designers, and more have come together to share their experiences with mental illness. In 2023, Speak Your Truth became a nonprofit with an aim to grow beyond one yearly event in Annapolis to other activities in the area. Find more information and get involved at speakyourtruthcrew.org.

14th Annual Lake Arbor Jazz Festival 

Join jazz enthusiasts from far and wide for the 14th Annual Lake Arbor Jazz Festival in Prince George’s County on July 17th through 21st. The festival will have an amazing lineup 30-plus artists and events including a pre-festival concert, the popular Summer White Affair, the Saturday outdoor jazz festival, and a Sunday jazz brunch. The festival will feature five days of smooth jazz and classic R&B with performances Avery*Sunshine, Gerald Albright, Queens of Jazz Soul featuring Althea Rene and Jeanette Harris, and many more. Find more information for the weekend of music you won’t want to miss at lakearborjazz.com.

Kent County 4-H Fair 

The Kent County Fair will be back at the Kent Ag Center in Chestertown, July 17th through 20th, celebrating 42 years. The fair features great food, 4-H and community exhibits, animals, tractors, games, and plenty of entertainment for the whole family. This year, enjoy a Power Wheels Derby for 3–8-year-olds and a pickle eating contest. If that isn’t intriguing enough, there will be a greased pig contest, livestock auctions, and an antique truck pull. The fair’s mission is to provide agricultural education and opportunities for the county’s youth. Find more information at kentcountyfair.org.

Plein Air Easton 

Celebrate 20 years of Plein Air Easton, the largest and most prestigious juried plein air painting competition in the United States. From July 12th through 21st, artists will create their paintings outdoors (en plein air), capturing the beauty of the local landscape of Talbot County. Fifty-eight artists are scheduled to gather, compete, and take place in other events, including at the Avalon Theatre in Easton. Find more information at pleinaireaston.com.

Big Band Night & Fireworks 

In celebration of Independence Day, the Chesapeake Bay Maritime Museum in St. Michaels will host Big Band Night on Saturday, July 6th beginning at 7 p.m. Guests are invited to bring lawn chairs and picnic blankets for an evening of music, dancing, and fireworks along the Miles River, featuring a performance from the Shades of Blue Orchestra at the historic Tolchester Beach Bandstand. CBMM’s waterfront campus offers a great vantage point to enjoy the St. Michaels fireworks, which begin at dusk that evening. The rain date for the concert and fireworks is July 7th. Tickets are on sale now at cbmm.org.

Benedictine Chrome City Fundraiser 

The Benedictine Chrome City Fundraiser will be July 27th on the Benedictine Campus in Ridgely. At the event, hundreds of motorcycles, hot rods, classic, custom, and vintage cars will bring together hundreds of people to support Benedictine. The Benedictine Foundation fosters relationships with people, foundations, and corporations by sharing Benedictine’s vital mission to support the special needs community. Find more information at benschool.org.