'Crab Cakes and Football, that's what Maryland Does!'

This oft quoted line from the movie Wedding Crashers, filmed aboard the Schooner Woodwind here in Annapolis, is a fitting tag line for our destination. In Annapolis alone you can watch Navy Football at Navy-Marine Corps Memorial Stadium and then walk to a local restaurant for the perfect Crab Cake Dinner.

But, come Fall, we're also known for an epic Bluegrass Festival on the shores of the Chesapeake Bay, the 2nd largest Renaissance Fair in the country, and of course the biggest and best in-water boat shows in the U.S.

There's always something new to explore in Annapolis & Anne Arundel County!

Maryland's Music Capital!

Annapolis is known as America's Sailing Capital, but we have much more to offer than sailboats and Chesapeake Bay sunsets. (Although they are pretty great).

The Annapolis Baygrass Music Festival, a two-day beach front festival, takes place September 30 & October 1 on the sandy shores of the Chesapeake Bay at Sandy Point State Park. Featuring 14 incredible bands like Yonder Mountain String Band * Railroad Earth * Keller & the Keels * Melvin Seals and JGB * Fruition * Lindsay Lou * and more! To see the complete schedule, hit the button below...

United States Boat Shows

It's officially Boat Show Season!

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 US Powerboat Show. Spend days exploring powerboats of all varieties and shopping for boat supplies, navigation equipment, and other marine accessories. 

October 12-15 – Annapolis Sailboat Show (Downtown Annapolis) If sailing is your style, the U.S. Sailboat Show is just three days after the Powerboat Show. From seasoned sailors to first-time boat buyers, this five-day event highlights new and premier boats. Check out educational opportunities for all skill levels, like the highly sought-after Cruisers University. Make plans today to maximize your time at the Boat Shows.

Fall Festivals

From North County to South County, our fall festivals bring in visitors from across the DMV with epic corn mazes, apple cannons, ghost tours, and hay rides... Learn More

Historic Hauntings

Celebrate Spooky Season with a ghost tour! Meet up with your spirited guide as they lead you through the dark alleys, spooky side streets, and lesser-known haunted sites of the old and creaky town of Annapolis ... Learn More

Tiffany Haddish

Emmy & Grammy award winner Tiffany Haddish brings her comedic stylings to an intimate and exciting show in Arundel Mills at Live! Casino & Hotel MD!... Learn More

Kunta Kinte Heritage Festival

The Kunta Kinte Heritage Festival has been rescheduled! Make plans to join us in Annapolis, October 28th for a full day of African American history, heritage, music, food, and family fun!... Learn More

Great Annapolis Pumpkins

You never know when these 1,000-pound pumpkins will pop up in downtown Annapolis, but they are hard to miss once they do! Presented by the Downtown Annapolis Partnership, the Annapolis Arts District, and co-sponsored by Visit Annapolis & Anne Arundel County, these gigantic gourds make for the perfect fall photo-op.

After you find them all, enjoy the rest of your day at a local Fall Festival or book a cruise aboard a tour boat! Fall on the Chesapeake Bay is the perfect time to sail and enjoy the colorful leaves from the water!

Winter in Annapolis

The holidays are just around the corner, and what better place to celebrate than in charming Annapolis, rated a Top Christmas Town by Travel & Leisure in 2022!

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. 

December 7, 14 & 21 – Midnight 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.

A Chocolate Binge Festival, our Historic Tree Lighting, and the Lighted Boat Parade are only a few things that set Annapolis & Anne Arundel County apart for the holidays. Explore more festivals and events and plan your winter escape on our website!

Download our Visitor Guide to begin planning your next getaway!