September in Annapolis is a time when the weather cools and leaves begin to change color over the Maryland State House, signaling the return of local seasonal festivals, one of the city’s favorite art events, and of course, Navy Football. Whether you explore historic Annapolis at your own pace – wandering the 300-year-old brick streets in search of its many hidden gems – or take up one of the suggestions below, September in Annapolis doesn’t disappoint.

Explore like a USNA Mid


September ushers in the return of Navy Football in Annapolis. Walk with the Midshipmen on the way over to the Navy-Marine Corps Memorial Stadium for a game, or pop into one of the town’s historic pubs and taverns to catch the game.

If history is more your speed, stop by the United States Naval Academy for a guided tour, a bite to eat, or to just mosey around the grounds, aka, “The Yard”. It’s a great way to spend an afternoon and it’s open to the public year-round (valid ID is required for anyone 18 and older). You’ll find impressive exhibits at the world-class USNA Museum; stunning architecture at Memorial Hall, Bancroft Hall, and the USNA Chapel; and an interesting lesson in naval history at the John Paul Jones Crypt.

Explore the Fringe


Now in its third year, the Annapolis Fringe Festival has become a staple event in the Annapolis Arts and Entertainment District on West Street. Packed with restaurants and art galleries, the first block of the street is closed off to cars for three nights (September 21-24), becoming a stage to actors, singers, magicians, poets, artist and acrobats.

The concept dates back to 1947 when, in Edinburgh, Scotland, it started as a street festival of unusual theater, dance and visual arts. Cities and towns around the world now celebrate with Fringe Festivals. It’s a great way to experience Annapolis’ growing, quirky arts scene.

Explore like a Local


Nothing says autumn like a fall festival. The tastes. The smells. The colors. Annapolis locals flock to four great fall festivals each year. The Maryland Avenue & State Circle Fall Festival (September 18th from 10:00 am – 5:00 pm) is held each September on historic Maryland Avenue. Packed with boutique/specialty stores and antique shops, vendors lining the street, along with two restaurants offering outdoor dining and live music happening throughout the day, the festival is a must for any September visitor and local alike.

On Saturday, September 17, the Annapolis Craft Beer and Music Festival offers a great way to close out the summer and get a jump start on Annapolis' fall festivities. Come experience over 120 beers from more than 45 regional and national craft breweries, live bands performing throughout the day, and brew seminars. This fun last-summer fling takes place at the Navy-Marine Corps Memorial Stadium from 12:00 p.m. to 6:00 p.m.

The Greenstreet Gardens Annual Fall Festival is a great way to get into the seasonal spirit. From September 17 - October 30, every Saturday and Sunday, bring the kids and let them loose in a giant corn maze, a blowup "jumping pillow", hay rides, a petting zoo, and rotating events for the whole family.

The Homestead Gardens Fall Festival (beginning September 24th) offers the perfect day out in the Annapolis Countryside with the family. Enjoy hayrides, a straw maze, pumpkin picking, BBQ, and live entertainment from 11:00 am to 4:00 pm every Saturday and Sunday through October 30th.

Explore the Chesapeake


With the fall quickly approaching, September is one of your last chances to get out on the water. Rent a kayak or paddleboard and take to the water (don’t worry if you fall in, the water is still warm). Climb aboard a sailing cruise to catch the sunset on the Annapolis Harbor. Rent a charter boat for the day and reel in some Rockfish (striped bass). If you’re planning on staying the night, there’s even a Boat & Breakfast where you can spend the night, being rocked to sleep by the Annapolis Harbor before waking up to a sunrise over the Chesapeake Bay.

If you're bringing the kids along, keep them entertained aboard the Sea Gypsy, a replicated pirate ship. Pirate Adventures on the Chesapeake offers boat tours for kids, where they're dressed up as pirates for the afternoon patrolling the Annapolis Harbor. Aside from thwarting other pirates with water cannons, the young pirates are also educated on the ecology of the Chesapeake, making for a fun, educational day on the Bay.

Explore the Flavors


Annapolis is known for its seafood, so why not experience what all the fuss is about this September at the Maryland Seafood Festival. Set against the Chesapeake Bay at Sandy Point State Park, the festival includes a variety of Maryland’s tastiest seafood dishes, live music, kids’ activities, vendor tents, and much more.

Dinner Under the Stars is still in full-swing as well. One of this summer’s most talked about events, Dinner Under the Stars takes place each Wednesday evening on the first block of West Street. Closed off to cars, the restaurants line the street with tables for patrons to dine under a blanket of lights. The event ends September 21st, so be sure to visit on the 7th or 14th to experience this great dining event.


Find more great September things to do by clicking here, or check out our local bloggers on Historian Annapolis and Foodie Annapolis.