A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of September. Event dates may be subject to change.
Maryland Renaissance Festival
Get ready to go back in time to 1536 at the 2022 Maryland Renaissance Festival in Crownsville. As always, there is plenty of entertainment, jousting, turkey legs, and of course, outfits. Visit the website for special promotions, events, and full calendar. The festival will go on from 10 a.m. to 7 p.m. on September 3rd through 5th, 10th and 11th, 17th and 18th, and 24th and 25th, as well as weekends in October. Find more information at rennfest.com
Maryland Seafood Festival
ABC Events is hosting the Maryland Seafood Festival on September 24th and 25th at Sandy Point State Park in Annapolis. This rain or shine event will host loads of seafood vendors, local shopping and vendor options, a fantastic beverage selection with lots of local craft beer, and tons of kids activities, all along the beautiful shores of the scenic Chesapeake Bay. Because of the limited availability of crabs and crab meat, be sure to pre-order crabs by September 15th. Find more information and pre-order crabs at abceventsinc.com.
Maryland Fleet Week & Flyover
The Maryland Fleet Week & Flyover Baltimore returns in-person and better than ever September 7th through the 13th at the Baltimore Inner Harbor, North Locust Point, Fort McHenry, Fells Point, and Martin State Airport. This bi-annual event was virtual in 2020 and hasn’t come together in person since 2018. This event celebrates the rich maritime traditions of the Chesapeake Bay and the contributions of Marylanders to the defense of the nation. There will be plenty of fleet week events including the flyovers, festivals, exhibits, and vendors stretching from the Maryland Science Center to the National Aquarium. This is a free and family-friendly festival. For more information, visit mdfleetweek.org.
Photo by Ken Tom
Blazers. Bourbon. Cigars.
Historic Annapolis is hosting their 9th Annual Blazers. Bourbon. Cigars. networking event at the William Paca House and Garden in Annapolis on September 29th from 6 to 9 p.m. Enjoy an evening of fine bourbon and whiskey tastings, beer and wine, along with cigars, delightful food from the area’s top chefs, and an array of vendors. There will be a VIP entry at 5 p.m. so be sure to get your tickets at annapolis.org.
Annapolis Run for the Lighthouse
Tie up your laces for the annual Annapolis Run for the Lighthouse at Quiet Waters Park in Annapolis on September 18th from 8 to 11 a.m. The Light House will provide a scenic half-marathon and 5K routes along the trails of Quiet Waters Park and through the beautiful Chesapeake Bay-front community of Hillsmere Shores. All proceeds from the race will benefit The Light House in Annapolis. Find more information and sign up for the race at annapolisrunforthelighthouse.org.
Photo by Cara Malfi Creative
Warriors in the Park
On September 10th, from 4 to 9 p.m., see Jimmie’s Chicken Shack, Pressing Strings, Honey Sol, and additional acts perform at Warriors in the Park at StageOne Park, the outdoor stage at MC3 in Annapolis. Bring your lawn chairs, umbrellas, blankets, and enjoy live music to honor the strong veteran community in Annapolis. In addition to the music, there will be a silent auction, multiple food and drink trucks, and local veteran organizations. Find more information at mc3annapolis.org.
Arts Alive Global
“Come Sail the World” at Arts Alive Global on September 9th at Maryland Hall. This year, Arts Alive, Maryland Hall’s single largest fundraiser of the year, is going worldwide. The campus will transform into a mini-globe with trips around the world through entertainment, décor, art, food, and cocktails. Find more information at marylandhall.org.
Annapolis 9/11 Heroes Run
The 2022 Annapolis 9/11 Heroes Run is scheduled for September 18th at 2 p.m. at the Navy-Marine Corps Memorial Stadium. Each year, local volunteers come together to organize this run in Annapolis and in 90 other locations around the world. This year, the run commemorates the 15th KIA Anniversary of Marine 1st Lt. Travis Manion and Major Doug Zembiec and the 10th KIA Anniversary of Navy Special Warfare Operator 1st Class Patrick D. Feeks. Register at 911heroesrun.org/Annapolis.
Anne Arundel County Literacy Council Book Fair
The 2nd Annual Anne Arundel County Literacy Council Book Fair fundraiser will be on September 24th from 10 a.m. to 4 p.m. outside Discoveries: The Library at the Mall at the Crate & Barrel Court in the Annapolis Mall. This fair will feature a large range of gently used books including children’s books, cookbooks, bestsellers, romance novels, memoirs, mysteries, thrillers, historical fiction, and more. Find more information at icanread.org/bookfair
Bay Bridge Paddle
September 25th is the Bay Bridge Paddle at Sandy Point State Park in Annapolis. Water enthusiasts of all ages and expertise are invited to the Paddle in the Chesapeake Bay. This race will bring together all levels of paddlers with multiple races available to support the Foundation for Community Betterment. Each race will present a different experience or challenge based on the bay’s shifting conditions. Find more information and sign up at abceventsinc.com.
Piney Orchard Street Festival
The 12th Annual Piney Orchard Street Festival will be back at 2400 Stream Valley Drive on September 10th from 11 a.m. to 6 p.m. The festival will have plenty of food vendors, as well as arts and crafts, franchise and general sales, ice cream, popcorn, beer, wine, entertainment, and so much more. Find more information at pineyorchard.com.
Boatyard Beach Bash
The Boatyard Beach Bash is back on September 10th from 5:30 to 10 p.m. Jimmy Buffet’s recording and touring band, the Coral Reefers, and other world-class musicians will perform to keep you in a Key West state of mind. The night will have great music, fantastic food, and signature cocktails on the scenic waterfront campus of Annapolis Maritime Museum in Annapolis. Find more information at amaritime.org or boatyardbarandgrill.com.
Microbrewery Festival
The 16th Maryland Microbrewery Festival is back on September 24th from 11 a.m. to 6 p.m. at Union Mills Homestead Park in Westminster. This festival celebrates and promotes the best of Maryland’s handcrafted and distinctive microbrews. There will be plenty of beer to be enjoyed, food vendors, live music, entertainment, and more. This event is the highlight of Carroll County Beer Week and proceeds of the festival will support Union Mills Homestead Foundation’s ongoing interpretation and preservation of the historic Union Mills site. Find more information at marylandmicrobreweryfestival.com.
Greenbelt Labor Day Festival
Since 1955, Greenbelt has hosted the largest all-volunteer organized event to raise funds to build a Youth Center and to celebrate Labor Day. September 2nd through 5th will be the 68th year of the festival at the Roosevelt Center in Greenbelt. The festival will have a book sale, craft fair, art show, pet show and more, as well as a parade on September 5th from 10 a.m. to noon. Find more information at greenbeltlaborday.com.
DogFest Washington D.C.
Celebrate our beloved pet dogs and the joy they bring to our lives. DogFest Washington D.C will have dog-friendly activities at Reston Town Square Park on Market Street between St. Francis Street and Explorer Street on September 24th from 11 a.m. to 3 p.m. This event supports the mission of Canine Companions to enhance the lives of people with disabilities by providing expertly trained service dogs free of charge. For more information, visit canine.org/dogfestwashingtondc.
Destination Prince George’s: Telling Our Story Through Public Art
Gather at Prince George’s Arts & Humanities Council on September 24th from 6 to 10 p.m. for Prince George’s Public Art event. The event will discuss the importance of public art and Prince George’s Arts & Humanities Council’s mission and dedication to integrating public art and urban design in the county. Find more information at pgahc.org.
Prince George’s County Film Festival
The Prince George’s County Film Festival is the premier program for new film works from up-and-coming and established independent filmmakers with diverse voices. The festival will take place September 22nd through 25th at the National Harbor and Bowie State University. There will be a 60-minute or longer narrative feature, a 60-minute or longer non-fiction work that educates, informs, or historicizes events and important figures (documentary), a 35-minute or shorter short film, and an animation of any length. Find more information at pgahc.org.
15th Annual St. Michaels Concours d’Elegance
Get ready for a day on the Eastern Shore full of grand classic motoring, classic wooden speed boats, fashion, and casual elegance along the Chesapeake’s Tred Avon River at the Talbot Country Club on September 25th. There will be plenty of food and beverage vendors. Find more information at smcde.org.
Paddling with the President
On September 21st, join Chesapeake Bay Maritime Museum President and avid paddler Kristen Greenaway in an evening of paddling along the Miles River and up Long Haul Creek. From 5:30 to 7:30 p.m., participants will have a chance to learn how to paddle and experience the beauty of our local waters. Register online at cbmm.org.
Chesapeake Film Festival
Celebrate the 15th Anniversary of the Chesapeake Film Festival with a weekend of provocative, insightful, and innovative films. There will be a live festival starting September 30th at the Eastern Shore Conservation Center followed by a week-long festival. Evenings of films will continue through October 2nd at Easton’s Avalon Theatre with outstanding films and conversations with the filmmakers. Plus, a virtual festival will go from October 3rd through 9th. Find more information at chesapeakefilmfestival.com.
Shaw Bay Raft-Up Concert
Bring your rafts, dinghy, paddle board, kayak, or sailboat to Shaw Bay along the Wye River for a relaxing day with music and a view on September 10th from 2 to 6 p.m. This free concert is held each year to raise funds and awareness for clean water efforts on the Eastern Shore of Maryland. For more information, visit shorerivers.org or email Freya Farley at ffarley@shorerivers.org.
Ride for Clean Rivers
September 18th will be the 17th ShoreRivers Ride for Clean Rivers. Cycle the beautiful back roads of Talbot and Queen Anne’s counties in support for ShoreRivers’ work for clean waterways. The ride will start at Chesapeake College and is a perfect way to finish the summer season. All proceeds go toward ShoreRivers’ science-based education, restoration, and water quality monitoring programs. For more information, visit shorerivers.org.
Haven Ministries Golf Tournament
Visit Queenstown Harbor Golf Course for Haven Ministries’ Golf Tournament on September 23rd to help benefit the homeless resource shelter. Enjoy a great day of golf while supporting Haven Ministries. There will be a shotgun start at 9:30 a.m. Register now or find more information at haven-ministries.org.
