Located in the heart of Maryland, Annapolis & Anne Arundel County is the ideal destination for welcoming fall. Cooler temperatures call to mind Navy football, fall festivals, and the U.S. Powerboat and U.S. Sailboat Shows! For a sneak peek at all that is going on this fall, check out the Visit Annapolis & Anne Arundel County website.


Tractor pulls people in a wagon an a farm
Bring the family to Annapolis & Anne Arundel County this Fall!
Image courtesy of Annapolis Discovered.


October 1Annual Agriculture Education Day (Davidsonville) – On a mission to buy local? Head to Y Worry Farm to meet with local farmers, craftsmen, and watermen, as well as local producers and local food trucks for a day of family-friendly ag education and food.  

October 1-2Annapolis Baygrass Music Festival (Annapolis) – Enjoy 14 bands on two stages during a beach-front festival that blends progressive bluegrass music with a core mission of protecting the Chesapeake Bay. The event at Sandy Point State Park features locally sourced food, including fresh oysters, regional microbrews, and wines, a ‘hopping’ beer garden, paddle boarding, kids’ activities, and more.  

October 1-23 (Saturdays and Sundays) – Maryland Renaissance Festival (Crownsville) – Journey back in time to the 16th Village of Revel Grove. Enjoy performances by more than 200 professionals on ten stages as you make your way around the 27-acre village. Applaud armored knights jousting on magnificent steeds in a 3,000-seat arena and mingle with the ‘locals’ in pubs and streets filled with knights, kings, queens, and village folk. Advance tickets are highly recommended.


power boats lined up in the water at a dock during the Annapolis Power Boat Show
October brings the United States Boat Shows to town.
Click here for more information on this year's shows.


October 2Lifeline 100 (Millersville) – Now in its 8th year, the Lifeline 100 Bike Ride highlights Anne Arundel County’s scenic trails and roadways. Cyclists of all ages and abilities are invited to choose the trail that is right for them – from 15-mile, 30-mile, 65-mile, and 100-mile options. Families out for a fun afternoon may opt for the 3-mile family fun ride during a fundraising event that promotes cycling awareness, bike safety, and the benefits of cycling.  

October 6-92022 United States Powerboat Show (Annapolis) – Celebrating 50 years, the United States Powerboat Show at City Dock invites boating enthusiasts to spend the weekend exploring a variety of new and used boat types including Bowriders, Center Consoles, Cruisers, Cuddy Cabins, Deck Boats, Power Catamarans, and more. It is an ideal event for purchasing boating supplies, navigation equipment, fishing gear, clothing, and marine accessories.  

October 7-31The Great Annapolis Pumpkins (Downtown Annapolis) – Come to downtown Annapolis in search of the Great Pumpkins! You cannot miss the 1,000-pound pumpkins that crop up in early October. Snap your picture with them using the hashtag #GreatAnnapolisPumpkins for a chance to win prizes from local businesses. The pumpkins will be carved into jack-o-lanterns just before Halloween!


Blue building with a giant pumpkin in front
The Great Annapolis Pumpkins make their historic return to Annapolis this October!
Image courtesy of Visit Annapolis & Anne Arundel County.


October 8 Chesapeake Arts Center (CAC) 8th Annual Arts in the Park (Brooklyn Park) CAC’s Arts in the Park free festival features live performances, art, more than 40 artists and community vendors, multiple hands-on art workshops for all ages, food trucks, and fun for the entire family. The all-ages community event runs from 10 am-3 pm and is free! 

October 8, 22, 29Navy Football (Annapolis) – Navy Football returns to Navy-Marine Corps Memorial Stadium in October. Click the link to learn more about Navy Football’s home game matchups against Tulsa, Houston, and Temple.  

October 8 National Cryptologic Museum (Annapolis Junction) – On Saturday, October 8, at 10:00 a.m., the National Cryptologic Museum (NCM) will host a Grand Opening Celebration that highlights the results of a two-and-a-half-year interior makeover. The museum now features all new layouts, displays, and many never-before-seen artifacts that played critical roles in protecting America’s national security. The museum that first opened to the public in 1993 is the National Security Agency’s principal gateway to the public. NCM transports visitors on a journey from the ancient world to the present day exploring the dynamic role cryptology has played in shaping our history.


A man with red rubber gloves shucks an oyster.
Enjoy fresh oysters at the Captain Avery Museum's 25th Annual Oyster Roast on October 15, 2022.
Image courtesy of Visit Annapolis & Anne Arundel County.


October 13-172022 United States Sailboat Show (Annapolis) – At a show in which virtually every major sailboat manufacturer is represented, seasoned sailors and first-time boat buyers can board and inspect most new models on the market, make side-by-side comparisons, and talk to industry representatives about all aspects of buying and owning a boat. The show provides sailing enthusiasts with the opportunity to connect with hundreds of boating gear and accessory exhibitors, fellow boaters, and television and social media sailing influencers.  

October 1525th Annual Oyster Festival at the Captain Avery Museum (Shady Side) –Gather for live music, a raffle, fun and games for the kids, and oysters! Enjoy oyster shooters and a raw oyster bar as well as favorites from Skipper’s Pier and Chesapeake Grille while listening to the sounds of the Eastman String and Polythene bands and performances by Kenny Holmes and Jonathan Stone from 12:30 p.m. until 5:00 p.m. Parking is available off-site (less than 1 mile) at Shady Side Park (1355 E. West Shady Side Road) with a courtesy shuttle. Rain date is Sunday, October 16.  

October 23Maryland Avenue Fall Festival (Annapolis) – Join the businesses of historic Maryland Avenue for the return of their annual Fall Fest, now in its 52nd year. Do not miss the ‘Halloween Pup Parade,’ live music and performances, fun for the kids, delicious food, a beer garden, unique jewelry and clothing vendors, antiques, and art, as well as fair trade, handmade, sustainable goods and so much more in the heart of Historic Annapolis!  

October 29Day of the Dead Festival | Día de Los Muertos Festival (Annapolis) – The City of Annapolis’ 4th annual Día de Los Muertos/Day of the Dead Festival at Maryland Hall features outdoor activities, food, vendors, and special performances from 4:00 p.m. until 9:00 p.m. Attendees are encouraged to dress up for the traditional holiday celebrated in Mexico and many Latin American countries. Come early to get a colorful sugar skull face painting at one of the multiple booths available.


Book a Haunted Pub Crawl or Ghost Tour this October.
Image courtesy of Reynolds Tavern.

October 1-31 Haunted Tours & Events (Annapolis) – With a town so old and historic, there are bound to be a few ghosts roaming the streets and taverns of ‘Old Annapolis Town’. Kick off the start of Spooky Season with an evening of haunted tales and ales with this list of ghostly adventures.  

October 1-31 Annapolis Tours & Crawls Ghost Tour (Downtown Annapolis) – Take a leisurely ghost walk through the historic downtown district on a spine-tingling journey into Annapolis’ dark and troubled history while meeting some of the City’s more spirited residents and visiting their most horrific haunted sites! Inquire about their Haunted Pub Crawls for a delightful evening of spirits and spirits!  

 October 1-31 Haunted Harbor Tours (Downtown Annapolis) – Schedule a nightly tour with Haunted Harbor Tours for a ghoulish adventure through the history and horror of Annapolis. Along the way, do not be surprised if you meet some of the City’s hauntingly memorable residents.  


But wait, there’s more!  


For more October events and Fall Festivals throughout Annapolis & Anne Arundel County, check out Visit Annapolis & Anne Arundel County’s events page and start planning your Fall Getaway today!