The Annapolis events calendar thrives on huge regional events and local favorites that always bring the crowds. When driving in, more guests choose Holiday Inn Express & Suites Annapolis over other Annapolis, MD hotels for a clean, affordable stay quick to the highway and everywhere they want to be. Experience one of these favorite annual Annapolis, Maryland events and festivals.

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Polar Bear Plunge | January

Annapolis Restaurant Week | February

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B&A Trail Marathon & Half-Marathon | March | Starts at Severna Park High School
The B&A Trail Marathon & Half-Marathon have been hosted annually in Severna Park, MA for over 20 years. Participation is fairly limited, so registered early if you wish to race.

Maryland Day Celebration | March | Celebrate Maryland's Birthday at cultural, heritage, enviromental and shopping locations in the Fours Rivers Heritage Area of Anne Arundel County Maryland.

Annapolis Oyster Roast | March | Annapolis Maritime Museum
Celebrate the coming of spring at this feast of the Chesapeake's most cherished bivalve. The seventh annual Annapolis Oyster Roast & Sock Burning, a fundraiser for the Annapolis Maritime Museum.

Annapolis Film Festival | March | The Annapolis Film Festival showcases over 70 films over 4 days

Annapolis Spring Sailboat Show | April | Multiple Venues on the Waterfront
Awesome multi-venue event that kicks off the spring and summer sailing season in 'America's Sailing Capital' with an opportunity to meet boat dealers, talk shop, demo new boats and win fun prizes – all admission FREE. Learn more about sailing in Annapolis, MD.

Annapolis Book Festival | April | Key School
Now in its fifteenth year, the Annapolis Book Festival is one of the premier community events in the region. Every year more than 3,000 people attended this free community Festival that celebrates the beauty, power, passion, and excitement of the written word.

U.S. Naval Academy Graduation & Commissioning Week | May | U.S. Naval Academy
A proud day for the Academy, the Midshipmen and their parents, and for Annapolis.

Chesapeake Bay Blues Festival | May

Annapolis Irish Festival | June | Anne Arundel County Fairgrounds
Celebrate everything Irish at the only festival of its kind in the region: The Annapolis Irish Festival,. Enjoy traditional Celtic music and Irish rock bands on three different stages, along with workshops and exhibits. When you get hungry, try some delicious Irish beef stew and other Irish favorites.

Paint Annapolis | June | Paint Annapolis is a week-long, juried plein air painting competition held in June, that brings to Annapolis painters from around the world.

Annapolis Art & Wine Festival | June | Navy-Marine Corps Memorial Stadium
The annual festival is a weekend of art, handmade crafts, wine tastings from over 25 Maryland wineries.

4th of July in Annapolis, MD | July 4 | Multiple Venues
In Annapolis, we do Independence Day big! Major 4th of July events in Annapolis include the Independence Day Parade, live entertainment at Market House and the City Dock, and finally the big Annapolis fireworks show. Head to the Spa Creek Bridge for a great vantage point.

Annapolis Crab Feast | August

Naval Academy Plebe Parents' Weekend | August | U.S. Naval Academy
The hardworking plebes, or freshmen, at the U.S. Naval Academy enjoy their first opportunity to visit with their families since Induction Day in early July. Includes a full weekend of activities.

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Maryland Renaissance Festival | August | September | October | Revel Grove in Crownsville, MD
For two months in the late summer, weekends belong to the Maryland Renaissance Festival. Guests drive in from all over the region to experience the nation's second largest Renaissance festival. Highlights include costumed performances, live jousting, and hearty fair food. Every weekend brings an exciting new theme and fun new attractions to discover. Costumes are highly encouraged, but live weapons are not allowed.

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Naval Academy Parents' Weekend | August | U.S. Naval Academy
A formal opportunity for midshipmen at the USNA to visit with their families during the semester. Parents have the opportunity to sit in on classes with the midshipmen, meet the superintendent and commandant, and more.

Seafood Festival | September | Sandy Point State Park
We're celebrating 50 years of food and fun at Sandy Point State Park with a weekend full of delicious seafood dishes, interactive cooking demonstrations, and exciting cook-off competitions!

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United States Sailboat Show | October | Marine Corps Memorial Stadium and City Dock
They don't call Annapolis 'America's Sailing Capital' for nothing. The United State Sailboat Show is the country's oldest and largest new, in-water boat show. No show has a wider and more diverse selection of vintage, modern and custom sailboats. The U.S. Sailboat Show is followed one weekend later by the United States Powerboat Show.

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United States Powerboat Show | October | Marine Corps Memorial Stadium and City Dock
Over three fast-paced days, more than 50,000 sailing fans will attend America's largest powerboat exhibition. The selection includes everything from luxurious yachts to high-speed monsters.

Oyster Classic | November | Navy-Marine Corps Memorial Stadium
The Annapolis Oyster Classic is an annual Maryland event featuring -- what else? Enjoy fresh oysters (several varieties) served grilled and on the shell. We've also got wine pairings, craft beer and cider.

Lights on the Bay | November – December | Sandy Point State Park
A dose of holiday magic comes to Sandy Point State Park. This drive-thru light show on the shores of the Chesapeake Bay makes for the perfect carriage ride. Popular with families and couples.

First Night Annapolis / New Year's Annapolis | December 31 | Annapolis Waterfront
Ring in the New Year with this festival celebration inspired by the 'First Night' events held all over the country. New Year's Annapolis is a special kind of New Year's Eve party, appropriate for families with children of any age.

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Sports at U.S. Naval Academy | Year-round | U.S. Naval Academy
The U.S. Naval Academy promotes one of the broadest athletics programs of any academic institution in the nation. Attend games at Navy-Marine Corps Memorial Stadium, Alumni Hall, and several other venues located within 3 miles of our hotel in Annapolis. View the USNA Athletics Schedule.

Traveling in with the team? Request a Proposal for special sports team rates.

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