There are so many exciting events happening in Annapolis this Fall – every weekend is an opportunity to enjoy a getaway to this historic city! Just imagine unplugging from the hustle and bustle of your day to day life, and escaping to centuries of historical charm, a lively waterfront, the energy of USNA football, and unique seasonal traditions. Annapolis’ active harbor provides a beautiful backdrop for everything from the famous boat shows to waterfront dining and sightseeing.
If you are planning a fall getaway to Annapolis, be sure to book your Airbnb with B4K in advance, and fill your calendar with some of these local favorites!
Maryland Corn Maze | Now–November 8
For a classic fall adventure, head to the Maryland Corn Maze in nearby Gambrills. The eight-acre maze is part of a larger farm experience with activities for families and visitors looking to spend a few hours outdoors. It’s a wonderful adventure to take for families!
The 2026 season runs September 12 through November 8 on select dates. Tickets are available, and visitors can check the maze’s calendar for specific operating days and times.
Annapolis Powerboat Show | October 8–11, 2026
Fall officially gets underway on the Annapolis waterfront with the Annapolis Powerboat Show. Along with the Sailboat Show, the Powerboat Show is one of the most iconic events happening in Annapolis each Fall! Held downtown at City Dock, the show brings boating enthusiasts together to explore powerboats, marine technology, gear, accessories, and the latest offerings from exhibitors.
Even if you are not shopping for a boat, the atmosphere is worth experiencing. The harbor comes alive with boats, visitors, vendors, interactive workshops, and maritime activity, making this one of the most exciting weekends of the year in Annapolis. Tickets are required for admission.
Annapolis Sailboat Show | October 15–18, 2026
One week later, the waterfront transforms again for the Annapolis Sailboat Show.
The harbor fills with over 350 boats to explore and discover. (There are even exciting world premieres of new models!) You can even attend. Shops, or take interactive courses. It is an especially memorable way to experience Annapolis because the event brings the city’s sailing heritage directly into the heart of downtown.
Spend the day exploring the show, then walk along the waterfront, enjoy dinner downtown, and take in the historic architecture surrounding City Dock. Tickets are required.
Spooky Walking Tours | October and Beyond
When Fall evenings arrive, Annapolis takes on a different personality! Spooky, ghostly tours lead visitors through historic streets while sharing colonial legends, eerie stories, and tales of the city’s haunted past. It’s a truly unique experience, with fun for visitors of all ages!
Several tours operate throughout the fall, with listings extending from October into December. Tickets or reservations may be required depending on the tour, so check with the individual tour operator before heading out.
Maryland Renaissance Festival | Weekends through October 25
Just outside Annapolis in Crownsville, the Maryland Renaissance Festival welcomes visitors into a colorful 16th-century village filled with jousting, performances, food, music, costumes, artisans, and plenty of merriment. This year marks and especially exciting return of the Maryland Renaissance Festival, as it celebrates its 50th anniversary!
The 2026 festival runs on select dates from August 29 through October 25, with October dates including October 3–4, 10–11, 17–18, and 24–25. Festival hours are 10 a.m. to 7 p.m., and tickets are date-specific and sold online.
USNA Homecoming: Navy vs. North Texas | October 24, 2026
Football fans have another great reason to visit Annapolis this fall. USNA Football is already back in action!
In addition to other home games on the schedule, Navy football fans will be descending upon Annapolis for the Homecoming Game, Saturday, October 24. In this year’s Homecoming Game, Navy will take on North Texas at Navy-Marine Corps Memorial Stadium. Kickoff is scheduled for 3:30 p.m.
Navy football weekends are one of the highlights of Fall in Annapolis! USNA alumni and superfans alike cite football at Navy-Marine Corps Memorial Stadium as one of the best events in Annapolis!
The Great Annapolis Pumpkins | October 24–November 2
Fall gets a little larger than life in downtown Annapolis with the Great Annapolis Pumpkins!
Giant pumpkins become part of the downtown landscape, creating fun photo opportunities and adding plenty of seasonal charm to an already picturesque historic district. Professional pumpkin carving is also part of the festivities, with the pumpkins remaining on display through November 2.
Take a stroll through downtown, grab a coffee, browse the shops, and keep an eye out for these enormous autumn creations.
Annapolis Scarecrow Stroll | October 24–November 2
Fall is packed with seasonal events happening in Annapolis that are great for the whole family! Local creativity takes center stage during the Annapolis Scarecrow Stroll. From October 24 through November 2, lamp posts lighting the streets and storefront windows will be decorated with creatively constructed scarecrows. Displays will be visible on West Street, Main Street, Maryland Avenue, and State Circle.
This easy, walkable activity is great fun for families with a range of ages, as little walkers will have fun looking at all the different scarecrows and older visitors will love popping into local boutiques, grabbing a coffee, and soaking in Annapolis’ historical charm.
Día de los Muertos | October 31
The list of amazing events happening in Annapolis is practically endless! In addition to seasonal festivities and iconic boat shows, Annapolis is also home to time-honored cultural celebrations. Join Día de los Muertos festivities, where residents and visitors alike will honor loved ones who have passed. Festivities include music, art, food, dance, altars, and beautiful community traditions. Festivities will take place at Maryland Hall, from 3 p.m. to 8 p.m. on Saturday, October 31, 2026!
The whole family will enjoy these festivities, as the area will come alive with traditional dance performances, live music, traditional food, and interactive activities for young visitors. Best of all, admission is free!
Thanksgiving Weekend | November 26–29, 2026
Visiting family in Annapolis for Thanksgiving? You will enjoy all the exciting holiday events happening in Annapolis! Explore downtown, enjoy waterfront dining, shop locally, and begin the holiday season with two beloved Annapolis traditions.
Saturday, November 28 is Small Business Saturday, making it a perfect opportunity to browse locally owned shops and find unique holiday gifts throughout downtown.
Then on Sunday, November 29, the Grand Illumination officially welcomes the holiday season with the annual tree lighting near Market Space and City Dock.
And if you want even more holiday magic, Lights on the Bay at Sandy Point State Park opens November 23 and runs through January 3, featuring more than 70 animated and stationary displays along a scenic drive beside the Chesapeake Bay.
See? If you’re excited to kick off the holiday season, Annapolis is the place to be!
Book Your Stay for these and Other Events Happening in Annapolis
As if that list above isn’t enough, there are even more exciting events happening in Annapolis this Fall. A weekend getaway to Annapolis can include additional Navy football games, tours of historic sites, holiday shopping, private boat excursions, hikes, and scenic trail walks throughout the area.
With so much happening, why make it a day trip?
Stay for the weekend. Explore at your own pace. Experience the history, waterfront, food, festivities, and seasonal charm that make Annapolis such a special destination.
And with your team of local experts ready to help you make the most of your stay, the choice is clear to book with B4K.