Autumn in Annapolis...there's nothing quite like it. It comes with a snap in the air and an energy that permeates the region—from the City Dock in downtown Annapolis to the fall festivals that stretch to the far corners of the Annapolis Countryside.

Many think summer is the best time to visit Annapolis—but autumn in Annapolis offers visitors all the fun of summer with fewer crowds and cooler temperatures. The water is still warm enough popular "summertime" activities like sailing cruises and kayaking/paddleboarding, and the crisp air makes for a perfect walking tour of the city or the United States Naval Academy. It’s also the season when of Annapolis cheers on the return of Navy Football. 


Dining options and nightlife fun don’t slow down with the changing of the seasons. Annapolis is known for its restaurants and summertime outdoor dining – whether on a rooftop patio, waterfront seating, or street-side table. Fall is the perfect time to take full advantage of the sunshine enjoying a meal before winter rolls into town. 

Spend the evening dining with the setting sun before enjoying a few drinks at one of the many historic pubs and taverns in town, or catch a live performance at one of a number of music venues downtown.

Autumn Dining in Annapolis

Autumn Highlights in Annapolis

In October, the whole county is gearing up for seasonal events, tours, and festivals. Regional favorites like the Maryland Renaissance Festival are in full swing, while other events like the US Boat Shows and Homestead Gardens’ Annual Fall Festivals round out the month. There is also still live theatre being performed in the courtyard at Reynolds Tavern. The Complete Works of William Shakespeare (Abridged), put on by the Annapolis Shakespeare Company (ASC) happens every Tuesday evening at 7:30 pm through September 26.

A great way to stay on top of all that’s happening during the fall is to check out our blogs. Get the latest dining news, tips, and ticks at Foodie Annapolis; things to do, see, and experience at Explorer Annapolis; and highlights on Annapolis and Anne Arundel County’s rich history at Historian Annapolis

Favorite fall events in Annapolis & Anne Arundel County:

Maryland Renaissance Festival (Through October)

When: Weekends and Labor Day, through October 22; 10:00 a.m. – 7:00 p.m.
Where: 1821 Crownsville Road, Annapolis

The region’s premier outdoor event and second largest Renaissance Festival in the country is celebrating its 40th season at Revel Grove. Travel back in time as you immerse yourself in the culture of a 16th-century English village, complete with King Henry VIII and his court. The festival includes 200+ entertainers, ten stages, a 3,000 seat jousting arena, 122 craft shops, 48 food and beverage emporiums, games, attractions and 85 acres of complimentary parking. Let merriment abound! 

Greenstreet Gardens Fall Festival

When: Saturday and Sunday, September 23 - October 29
Where: Greenstreet Gardens, 391 West Bay Front Road, Lothian, MD 20711

Six weekends of fall festivities is back and even better than before! Come enjoy different themed events and activities each weekend with family and friends. Our 5-acre corn maze, pumpkin bowling, jumping pillow, haunted hay ride, cow train, giant teepee, corn box, straw castle, underground slide and more - is everything you could ever imagine!

Greenstreen Gardens Corn Maze

Homestead Gardens Annual Fall Festival

When: Weekends, September 23 through October 29, 11:00 a.m. to 6:00 p.m.
Where: Homestead Gardens, 743 West Central Avenue, Davidsonville

Homestead Gardens' Annual Fall Festival is the largest in the area! Enjoy this family tradition featuring 15 rides and attractions, demonstrations, entertainment, food and beverages – including Homestead’s world famous apple cider doughnuts. New This year is our Midway and the Midway Bee Stage in the nursery where you will find special shows and music geared to families, the pumpkin express’s “cousin” the Bee Express, carnival games under the tent, sweet treats and more.  In our lower field we have live music on the main stage, our pipe slide, straw maze for the little ones, corn holes, the new “human Bowling ,” delicious food and beverages at Homestead’s “Grab & Go,” and Kona Ice.

U.S. Sailboat Show

When: Thursday-Monday, October 5-9; 10:00 a.m. to 6:30 p.m.
Where: City Dock, Annapolis

Now in its 47th year, the nation’s oldest and largest in-water sailboat show featuring exclusively new boats attracts more than 50,000 boating enthusiasts from around the world to America’s Sailing Capital each year. The event is recognized worldwide as the premier sailing showcase for seminars, boating attire and accessories, foul weather gear and boats of all sizes. 

U.S. Powerboat Show

When: Thursday-Sunday, October 12-15; 10:00 a.m. to 5:00 p.m.
Where: City Dock, Annapolis

Now in its 45th year, the nation’s oldest and largest in-water powerboat exhibition features everything from luxurious motor yachts and trawlers to high-performance boats and offshore fishing machines. The show includes family cruisers, center consoles, inflatables and the world's largest power catamaran section. Attendees will also find a wide selection of marine equipment, high-tech electronics, accessories, gear, and related services.

Historic Ghost Walks

When: October 6-28, Fridays & Saturdays, 7:30 pm & 8:00 pm.
Admission: Adults $22, Children 3-11 $14

Get in the Halloween spirit with a historic Ghost Tour through historic downtown Annapolis. As the sun sets and darkness descends upon the timeless streets of Annapolis, follow your spirit guide who will share stories of drowned watermen and other spirits that forever linger in the mist. Annapolis Tours by Watermark offers Historic Ghost Walks at dusk from Spring through Fall. During the month of October, the tour includes an exclusive tour inside the haunted Big Brice House! A period dressed guide will lead you by candlelight through the haunted streets of Annapolis.