Image courtesy of Christian Smooth.
Kunta Kinte Heritage Festival
Navy/Marine Corps Memorial Stadium, Annapolis, Maryland
September 14
In September 1987, the Kunta Kinte Celebration started in Annapolis, Maryland. Today known as the Kunta Kinte Heritage Festival, the festival celebrates the perseverance, education, and cultural heritage of Africans, African Americans, and Caribbean people of African descent. Stay tuned to discover what musical, comedic, and fashion performances will light up the Main Stage with positive energy. Learn more about the Kunta Kinte Heritage Festival and how it enriches your weekend in Annapolis & Anne Arundel County with black cultural experiences.
Annapolis Songwriters Festival
Headline Stage: City Dock; Venues throughout Downtown Annapolis
September 14 - 15
The multi-day music festival takes place September 12-15 throughout Downtown Annapolis, with artists performing at the City Dock stage located in Downtown Annapolis at Susan Campbell Park. Free events will occur in bars and restaurants throughout Downtown Annapolis along the 'Songwriters Trail' from Westgate Circle to City Dock. Other ticketed venues include Rams Head On Stage, and Maryland Hall. Make this festival a weekend to remember and begin planning your Annapolis and Anne Arundel County adventures.
Image courtesy of Maryland Renaissance Festival and Stacy Sutton.
Maryland Renaissance Festival
1821 Crownsville Road, Annapolis, Maryland
September 1, 2, 7, 8, 14, 15, 21, 22, 28, 29
October 5, 6, 12, 13, 19, 20
Enter the 16th century enchantment of Revel Grove, a 27-acre village presided over by King Henry VIII. From August to October, feast and dress-up with Lords and Ladies from near and far at one of Maryland’s most anticipated celebrations –The Maryland Renaissance Festival! With plenty of time to revel in festivities, you will want to journey to the 18th century just moments away in the charming, walkable downtown Annapolis area. There, 300-year-old buildings now house restaurants, lodging, and shopping, perfect for a weekend-long adventure.
Maryland Seafood Festival
Sandy Point State Park
September 14-15
Honestly, who can resist the delectable taste of fresh Maryland seafood? The Maryland Seafood Festival has been showcasing great seafood, live entertainment, bay themed crafts, chef demos, and crab soup cook-offs for decades! You won’t want to miss exclusive deals like The Naptown Seafood Sampler. This sampler includes 8 samples from local area restaurants along with a drink (beer, water, soda) for only $25. Or enjoy the Beer & Oyster tastings featuring the most delicious oysters from the Chesapeake Bay region. Get ready for a weekend foodie adventure and stay minutes away from the festival at the Crown Plaza Annapolis where you can find a discounted stay!
Image courtesy of Jay Strausser.
Annapolis Baygrass Festival
Sandy Point State Park
September 21st & 22nd
Every jam saves the Bay at Annapolis Baygrass Festival! Baygrass is a conservation and community-focused musical event that blends the finest progressive bluegrass, jamgrasss, and Americana music with an incredible beachfront venue, and a mission to protect the Chesapeake Bay while raising mental health awareness. Be a part of a good cause and enjoy 14 of the best local and nationally touring bands on two alternating stages in the sand at Annapolis’ Sandy Point State Park. This fall weekend in Annapolis is a true Chesapeake treat featuring fresh oysters, microbrews, wines, beach yoga, kids’ activities, mental health workshops, and more!
Image courtesy of Corrigan Sports.
Bay Bridge Run
Chesapeake Bay Bridge, near Annapolis, Maryland
November 10, 2024
Run, don’t walk, actually you can do both-to your only chance at walking or running crossing the majestic Chesapeake Bay Bridge which is typically closed to pedestrians. The Bay Bridge Run is an annual 10K race that traverses the Bridge’s eastbound span from Anne Arundel County to Kent Island in Queen Anne’s County and finishes with a huge post-race party! Whether you race, spectate, or volunteer, you’ll be on your toes excited for an unforgettable experience. Get your best racing shoes ready and pack your bags for an active weekend away with the most stunning hotel views of Annapolis and Anne Arundel County. Book your stay with one of these unbeatable rates.
The Chesapeake Bay area is always buzzing with fall festivities, perfect for all ages. Learn more about upcoming festivals and holiday events by visiting the full event calendar. Happy fall getaway planning!
