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Local Events

Annapolis Events and Festivals in Maryland

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 Hotel & Suites 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.

Look for even more events on our blog >>

things to do in annapolis

B&A Trail Marathon & Half-Marathon
March 30, 2014 | 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.

Annapolis Spring Sails Event
April 25-27, 2014| 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.

U.S. Naval Academy Graduation & Commissioning
May 23, 2014 | U.S. Naval Academy
A proud day for the Academy, the Midshipmen and their parents, and for Annapolis.

Annapolis Nautical Flea Market
May 2014| Navy Marine Corps Stadium
One of the largest flea markets in the nation dedicated to sailing, boats and nautical equipment. Along with the humongous show area, the Flea Market includes demos, events and seminars.

4th of July in Annapolis, MD
July 4, 2014 | 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 events

Maryland Renaissance Festival
August – October 2014 | 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.

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.

Naval Academy Parents' Weekend
August 7-10, 2014 | 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.

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United States Sailboat Show
October 9-13, 2014 | 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.

United States Powerboat Show
October 16-19, 2014 | 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.

Metric Marathon
September 21, 2014 | Southern High School
The beginning of fall is the perfect time for this annual marathon hosted in Harwood, Maryland.

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.

Rosaryville Veteran's Day 50k
November 8, 2014 | Rosaryville State Park
Commemorate Veteran's Day with this annual run starting at Rosaryville State Park in Upper Malboro, MD.

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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