As the days grow shorter and the leaves begin to fall, Autumn makes itself known along the shores of the Chesapeake Bay. In October, Annapolis & Anne Arundel County always has something to do. The picturesque Annapolis waterfront comes alive with the sight of sailboats & powerboats from around the world at the U.S. Sailboat Show & Power Boat Show.

Cozy coffee shops and bookstores are brimming with character and a hint of pumpkin spice as they draw in passersby in town for Navy Football and the Annapolis Bagrass Music Festival! Fall Festivals with epic corn mazes and the Great Pumpkins (close to 1,000 pounds each) start popping up across the county. Fall looks good on us, and we can't wait to show you what's in store for visitors during their stay in Annapolis & Anne Arundel County this season!


A graphic with a lineup of musicians for the Annapolis Baygrass Music Festival


Weekends in October 

Weekends in OctoberMaryland Renaissance Festival(Crownsville) Hear ye! Hear ye! Step into the 16th-century Revel Grove and leave your modern woes behind. RennFest has something for everyone. From turkey legs to toasting with mead to jousting and cheering on your own Kingdom, it is no wonder this immersive experience is one of Maryland's most extravagant and popular events.      


September 30 & October 1Annapolis Baygrass Music Festival (Sandy Point State Park) Every jam saves the Bay! Sit on the shores of the Chesapeake Bay at Sandy Point State Park and enjoy two days of the best bluegrass music around. Bands playing include Yonder Mountain String Band, Railroad Earth, and artist at large Lindsay Lou. The whole family is welcome at this festival!  


October 5-8 – Annapolis Powerboat Show (Downtown Annapolis) The City Docks of Annapolis will buzz with excitement as boat lovers from around the globe return to celebrate the 50th anniversary of the U.S. Powerboat Show. Spend days exploring powerboats of all varieties and shopping for boat supplies, navigation equipment, and other marine accessories.   


October 6 & 7Broadway in Annapolis (Annapolis) Get ready for the wickedly funny and timeless musical 'They're Playing Our Song' at Maryland Hall from Tony Award-winners Marvin Hamlisch and Neil Simon. It's a limited local run you don't want to miss. It's an evening of fun when you pair music with laughter.  


A walkway into a floating in water boat showe with flags flying in the air.
Discover why sailing and boating enthusiasts descend upon Annapolis every October for the United States Boat Shows!
 Image courtesy of VAAAC.


October 12-15 – Annapolis Sailboat Show (Downtown Annapolis) The U.S. Sailboat Show is just three days after the U.S. Powerboat Show—this annual celebration of sailing features floating docks lined with sailboats from manufacturers worldwide. Peruse multihulls, monohulls, cruisers, racers, sailing dinghies, and more. Show tents line the shore, stocked with the latest in nautical gear and accessories, electronics, communication equipment, sails, rigging, education, charter companies, clubs, and more!     

Fall Fun for All  

Weekends (and some weekdays) in OctoberMaryland Corn Maze (Gambrills) It is time to get lost in the great outdoors! Swing by Gambrills to test your luck at the Maryland Corn Maze, indulge in some of Fall's finest treats, and take a hayride! Plus, this is your one-stop shop to pick a pumpkin, too!    


Weekends (and some weekdays) in OctoberSpecial Historic Hauntings Walking Tour (Annapolis) Your spirited guide will lead you through the dark alleys, spooky side streets, and lesser-known haunted sites throughout Annapolis. Hear diary entries and newspaper articles of what frightened early 18th-century folks. Who knows, after this haunted walk…your own story may be added to the history of Annapolis.  


October 1 - 31Great Annapolis Pumpkins (Annapolis) Search Annapolis for the Great Pumpkins! You cannot miss these 1,000-pound pumpkins that crop up in early October. Snap your picture with the plump pumpkins and share them on social media using the hashtag #GreatAnnapolisPumpkins. Even better, the pumpkins will magically turn into carved jack-o-lanterns just before Halloween! Follow us on social media @VisitAnnapolis so you do not miss the Great Carving!  


October 8Fall Harvest Festival Featuring War of 1812 Remembrance (Pasadena) Learn about African Americans during the War of 1812 and their contribution to Hancock's Resolution. Plus, participate in classic fall family activities like scarecrow making, corn husk doll making, and games. Performing at the festival is The Chanteymen, a renowned group of singers of old-time sea chanteys.  


A Giant Green pumpkin in top of a hay bale in front of a church.
You can't visit Annapolis in the Fall without a stroll through town in search of the Great Pumpkins!


October 20 – November 1 – Scarecrow Stroll (Annapolis) For eleven days, scarecrows will line historic West Street, created by teams, schools, and businesses from across Anne Arundel County. Previously dressed up as Midshipmen, and even a mom out on a spa day, these creative scarecrows will compete for votes starting October 21 at Fall Fest on West! 


October 21 – Fall Fest on West (Annapolis) Enjoy live music, pumpkins, events for kids, and more at this year's Fall Fest on West. Dinner Under the Stars returns to West Street for the night, so have some fun, then grab a great bite to eat under the twinkling canopy of lights. The Annapolis Corgi Club Parade is a classic Fall Fest creature feature that you must catch while attending!  


October 22 – Maryland Avenue Fall Festival (Downtown Annapolis) This classic Annapolis event is one for the entire family to enjoy! Join the businesses of historic Maryland Avenue for the return of their annual Fall Fest featuring the infamous Halloween Pup Parade, live music, performances, Halloween-themed activities for the kids, great food, a beer garden, and so much more! Don't forget to shop for local goods while you're visiting.


All October Long – Visit an Anne Arundel County Farm or Fall Festival (Countywide) The fall season isn't complete until you've spent the day at a local farm or fall festival. Pick a pumpkin, shop for fall décor, and enjoy a Fall Festival at one of Anne Arundel County's best farms, gardens, and nurseries, including Homestead Gardens, Greenstreet Gardens, Knightongale Farms, and Doepkens Farms.


Two women jump on a jumping pillow at a Fall Festival
Get out and explore all the fall festival fun in Anne Arundel County this October!


Local Festivals & Events  

October 1 – Lifeline 100 Bicycle Event (Millersville) This 9th annual event brings in cyclists of all ages and abilities from around the Mid-Atlantic to showcase Anne Arundel County's scenic trails and roadways all while spotlighting cycling, safety, and its benefits for all. The 15-mile ride raises money for local non-profits. The 100-mile course begins at the BWI Loop and winds through scenic countryside and the Chesapeake Bay, all the way down to Southern Anne Arundel County. Lifeline100 has raised over $300,00 so far in this thrilling Anne Arundel County century ride. 


October 1 – Paint Your Way to a Cleaner Bay (Shady Side) Adults and kids can give back to the Chesapeake Bay with the Captain Avery Museum and their exciting, family-friendly activities. Learn about oysters, oyster habitats and their decline, and how stormwater management at home can help. Then, adults will paint rain barrels to take home, while kids will paint tree stumps with scenes of Chesapeake Bay creatures and plants, which will then become seats for an outdoor classroom. This Chesapeake Bay fun is free for all those who register. 


October 4 - 7 – Riviera Beach VFC Fall Carnival (Pasadena) Head on over to Midway at the Riviera Beach VFC Carnival, where games and rides await! Enjoy delicious food and drinks with the entire family. Come one night or come all!


Bay bridge views for lifeline 100 bike riders
Learn more about the Lifeline 100 Bike Race on their website.
 Image courtesy of Bike AAA.


October 7 – Navy Football vs. North Texas (Annapolis) It's a showdown between Navy and North Texas at Navy-Marine Corps Memorial Stadium. The Midshipmen kick off at 3:30 PM, giving you plenty of time to set up your tailgate and enjoy football in the Fall.  


October 8 – Hands-On History Day (Annapolis) Drop into the Museum of Historic Annapolis to learn about portrait miniatures, or as kids these days call them, "selfies"! These historic portraits represent tokens of loyalty, friendship, and love, and now families will be able to create their own while learning about Annapolis' history.  


October 8 – Comedian Tiffany Haddish (Hanover) Plan your weekend getaway at Live! Casino & Hotel Maryland around Emmy and Grammy winner Tiffany Haddish's comedic performance. You've seen her in movies and on television; now see her on stage at The HALL at Live! Shop, dine, and play at Arundel Mills while you're waiting for doors to open for this one-night-only event!  


October 13 – Maryland International Agriculture and Environment Conference(MDINTAG) (Edgewater) Hosted at the Smithsonian Environmental Research Center, the mission of this international conference is to highlight timely global topics, share best practices, and bring together the best and brightest minds in the agriculture and environmental sectors. MDINTAG cultivates the importance of regenerative farming, developing partnerships, and NextGen youth. 


The concert hall with people in the audience and performers on stage
The HALL at Live! welcomes Tiffany Haddish!
Image courtesy of the HALL at Live!


October 14Captain Avery Oyster Festival (Shady Side) This annual waterfront festival boasts community company, fine regional music, local food and drink, and oysters! This Best of the Bay award-winning festival has been going on for 26 years in Anne Arundel County. Admission is $10 for members, $15 for non-members, and free for kids under 13. The rain date is scheduled for Sunday, October 15. 


October 14 Art @ the Park (Quiet Waters) Visit one of Anne Arundel County's waterfront parks and enjoy live music, demonstrations, and art in one great place. The wide variety of art on display and for purchase includes ceramics, jewelry, woodworking, paintings, and photography. Bring the whole family and the dog too! 


October 14 Celebrating Indigenous Peoples' Day (Linthicum) In honor of Indigenous People's Day, the Benson-Hammond House is bringing out the Schramm Farm Collection of art and artifacts. This previously retired collection is one you have to see. The museum will be open from 11 AM – 3 PM and is $7 for adults, $3 for kids 6-15, and kids 6 and under are free.  


October 20Comedian Paul Reiser (Annapolis) Comic, actor, television writer, author, and musician Paul Reiser is coming to town with two evening performances at Rams Head On Stage. Enjoy dinner at Rams Head Tavern before stepping into an evening of laughs. Both shows are 21+.  


Arundel Ambassador - Quiet Waters Park
Celebrate Art in the Park at Quiet Waters Park!


October 21U.S. Naval Academy Football vs. Air Force (Annapolis) It's a showdown between Navy and Air Force! The Midshipmen take the field against the Falcons at noon for this military rivalry game! Spend the night in Annapolis the night before and check out one of these great places to grab breakfast before heading into Navy-Marine Corps Memorial Stadium.  


October 27Summer Drive-In Movies Under the Stars (Bay Ridge) Just because it's Fall doesn't mean you can't watch a movie outside under the stars! Pack up the family with blankets, food and drink, and some chairs, and enjoy a free showing of "Corpse Bride" to celebrate the Halloween season. This event is free for everyone.    


October 28Stories & Art in the Galleries (Brooklyn Park) Come to the Chesapeake Arts Center for a bilingual family program for kids ages 2-6. Enjoy the enchanting story of "Gustavo, the Shy Ghost" and participate in a paper mâché sugar skill activity from 10-10:45 AM.  


October, Various DatesBaltimore Orioles Baseball (Arundel Mills / BWI Districts) October baseball is back in Maryland! Stay and play in the Arundel Mills and BWI districts and take the MARC train straight to Camden Yards, home of the Baltimore Orioles, who are on the path to the 2023 World Series. You can't spell October without The O's!


SPCA Lights on the Bay is a Winter in Annapolis Highlight!
A light display with reindeer spelling out 'Lights on the Bay'
Lights on the Bay is a winter tradition!

Looking Ahead - Save the Date for Winter in Annapolis!

Consistently ranked as a top-tier Christmas Town in the U.S.!


November 12 Bay Bridge Run (Chesapeake Bay) The Bay Bridge Run is a 10K race that traverses the eastbound span of the Chesapeake Bay Bridge from Anne Arundel County to Kent Island in Queen Anne's County and finishes with a huge post-race party! Once a year, the bridge shuts down traffic on the eastbound span for a race that tests your mettle and your fear of heights! The views and photo ops abound, and this race is bringing in race enthusiasts from across the country.   


November 19 – January 1 Lights on the Bay (Sandy Point State Park) There's no better way to get the whole family into the holiday spirit than cruising along the shores of the Chesapeake Bay during Lights on The Bay, November 19, 2023, through January 1, 2024. Weather permitting, the electric wonderland will be on full display nightly from 5:00 PM to 10:00 PM at  Sandy Point State Park. Take a night - or a couple of nights - to enjoy the electric show from the warmth of your car. 


Runners running across the Chesapeake Bay Bridge
Conquer this epic 10K and your fear of heights on November 12, 2023!


December 7, 14 & 21Midnight Madness (Annapolis) Don't miss Midnight Madness, where select stores in downtown Annapolis along Main Street, Maryland Avenue, and West Street remain open until midnight (11 PM on December 21), giving bargain-hunters and last-minute shoppers an excuse to get out and shop well into the night. Stores pull out all the stops with holiday displays, treats, and special discounts and sales for holiday shoppers.


December 9Eastport Yacht Club Lights Parade (Eastport) The magical Eastport Yacht Club Lights Parade takes place along the Annapolis Harbor and Spa Creek on the second Saturday in December every year. This annual tradition has been delighting holiday revelers for 40 years! View the parade from the water on your own boat, a tour boat, or charter a boat to experience the holiday spectacle from the water. Or gather with friends and family along the neighborhoods of Eastport and Annapolis, where every street ending at the water offers up a perfect view!