Annual Events & Festivals in Anne Arundel County

March 2, 2024

Our region is home to a lively annual calendar of festivals, events, parades, and more. Visit our Events Calendar to view a full list of lectures and public programs as well.


Annapolis Film Festival

The Annapolis Film Society and Film Festival

The Annapolis Film Festival and Annapolis Film Society bring together a diverse cross-section of our community and beyond for a shared cinema experience that enlightens, entertains, and inspires, sparking conversation and connection within our community. The Annapolis Film Festival showcases more than 70 films over four days, and features panel discussions, post-screening Q&As, coffee talks, and more with filmmakers, directors, and industry experts each year.

Maryland Day Celebration Weekend

Chesapeake Crossroads Heritage Area

The Maryland Day Celebration commemorates the formal founding of the colony of Maryland. Maryland Day Celebration Weekend is a unique heritage-based group of events in Annapolis and southern Anne Arundel County. Maryland Day celebrations in Annapolis and Anne Arundel County are a hit with family and friends getting together to experience the local history, culture and heritage of the region. Many know we have the signers of the Declaration of Independence calling the area home, regional arts destinations like Maryland Hall and our rich maritime history with the Chesapeake Bay but we have a lot of great surprises you might not be aware of. Plan to visit Annapolis for the Weekend as we open our doors to over 40 locations for free or just $1 and give you fun affordable reasons to experience the area with all your friends and family.

St. Patrick’s Parade and Weekend

Naptown Events

Celebrate the luck of the Irish in the heart of historic Annapolis, Maryland, during the much-anticipated St. Patrick’s Day Weekend! The weekend is filled with vibrant festivities, live music, and a lively atmosphere that will transport you to the Emerald Isle.


Annapolis Spring Sailboat Show

Annapolis Boat Shows

Every April, the Annapolis Spring Sailboat Show returns to the historic seaport town of Annapolis to showcase new and brokerage boats including catamarans, monohulls, family cruisers, daysailers, and inflatables. Guests are invited to meet with boating clubs and charter companies, shop gear and equipment, and ring in the new season with fellow sailors and marine professionals. With live entertainment, seminars, and a festive tasting tent, the fun lasts all day. As the show winds down, guests may visit the wide variety of restaurants, shops and bars just a few steps from the show gates.


Commissioning Week

United States Naval Academy

Celebrate the graduation of the United States Naval Academy with a variety of events from a performance by the Blue Angels to guided tours of the Academy. View the Commissioning Week schedule

First Sundays Arts Festival

Inner West Street Association

From May through November, part of inner West Street is closed to allow thousands of visitors to enjoy shopping for unique arts and crafts from over 130 vendors. Visitors can also enjoy live music and café-style dining. Visit the First Sunday Arts Festival website

Dinner Under the Stars

Inner West Street Association

From May to September, the first block of Annapolis’ historic West Steet is where families and friends meet Wednesday and Saturday evenings to relax, dine under the stars, dance, and enjoy live music. When the summer sun sets, a canopy of overhead lights adds romance to every evening of Dinner Under the Stars, where participating restaurants will give you a wide choice of international and hometown flavors.

May Day

The Garden Club of Old Annapolis

May Day is one of the most beautiful days in Annapolis. On May 1st the doors of homes and businesses in our centuries-old City of Annapolis are adorned with baskets full of fresh-cut flowers and colorful ribbons. What began as a Garden Club of Old Annapolis Towne beautification project in 1956 has grown into a tradition in which residents and business owners compete for winning ribbons and an invitation to the Garden Club’s Annual Tea.


Annapolis Juneteeth Parade and Festival

Celebrate Annapolis Juneteenth Corporation

The mission of the Annapolis Juneteenth Celebration is to commemorate the emancipation of the last enslaved Africans in the United States. On June 19, 1865, Union troops arrived in Galveston, Texas to enforce the Emancipation Proclamation. Although the Emancipation Proclamation had been issued over two years prior, the news was withheld from many enslaved Africans. Today, celebrate the freedom and continued legacy of resistance, empowerment, and community building with a free parade and festival in Downtown Annapolis.

Annapolis Pride Parade & Festival

Annapolis Pride

Annapolis Pride celebrates the LGBTQ+ community, engaging local residents, businesses and groups to unite in welcoming and embracing diversity in Annapolis. Join them in the heart of historic Annapolis for a vibrant and inclusive event to celebrate love, equality, and diversity at the Annapolis Pride Parade and Festival.

Paint Annapolis

Maryland Federation of Art

Paint Annapolis is an internationally juried Plein air painting competition hosted by the Maryland Federation of Art. For over two decades, Paint Annapolis has been a premier outdoor painting event, that brings together artists and patrons from across North America and Europe to be a part of our community and celebrate the city where colonial architecture meets maritime heritage. Artists are invited to submit three of their best plein air works and apply to be a juried artist to paint our beautiful historic town, exhibit your work in Circle Gallery, and compete for cash awards.


Fourth of July Naturalization Ceremony

Historic Annapolis

Begin your 4th of July morning with an inspirational Naturalization Ceremony on the outdoor terrace of the William Paca House and Garden, when people from communities around the globe become our nation’s newest citizens in a ceremony conducted by officials from U.S. Citizenship and Immigration Services. The Naturalization Ceremony is free and open to the public.

Fourth of July Weekend

City of Annapolis

The City of Annapolis celebrates Independence Day with a parade and fireworks on Tuesday, July 4, 2023. The parade begins at Amos Garrett Boulevard and proceeds along West Street, around Church Circle, and down Main Street. Following the parade, the Salvation Army James B. Anderson Conservatory Band performs patriotic music at Annapolis City Dock. The fireworks display begins at approximately 9:15 p.m.


Annapolis Rotary Crab Feast

Rotary Club of Annapolis

Held at the Navy-Marine Corps Memorial Stadium, the Annapolis Rotary Crab Feast is an evening of crabs, barbecue, corn-on-the-cob, and plenty of beverages on a beautiful summer evening.  Since 2005, the Rotary Club of Annapolis has awarded over $1 Million Dollars in grants via the Crab Feast grant program and the proceeds from the event are donated to local charities.


Annapolis Songwriters Festival

Rams Head

Modeled after the hugely successful Key West Songwriters Festival, the largest festival of its kind in the world, the Annapolis Songwriters Festival brings our love for music to the bay! Like Key West, Annapolis has its own world-renowned watering holes and intimate theater settings, making our historic capital on the bay the perfect setting for live music enthusiasts to get acquainted with the faces, voices, and stories behind the songs.


Annapolis Boat Shows

Annapolis Boat Shows

For over fifty years, the Annapolis Boat Shows have produced in-water sail and powerboat shows where boaters may board the latest boat models, research and purchase boating equipment, foul weather gear, electronics, nautical education, charters, and everything else a boater or boat owner needs. First is the Annapolis Powerboat Show, followed the next weekend by the Annapolis Sailboat Show. Seasoned and novice sailors alike are invited to expand their horizons and connect with fellow sailors during this internationally acclaimed show.

Great Annapolis Pumpkins

Downtown Annapolis Partnership

Appearing just after the first weekend in October, Visitors strolling through downtown Annapolis and the Annapolis Arts District will find gigantic pumpkins at multiple locations. Take your picture with real pumpkins that are over 1000 pounds each and post pictures to your favorite social media pages for chances to win prizes from local businesses.

Kunta Kinte Heritage Festival

Kunta Kinte Celebrations, Inc.

Kunta Kinte was one of 98 enslaved people brought to Annapolis, Maryland aboard the ship Lord Ligonier in 1767, and despite many years in bondage, he never lost his connection to his African heritage. Kunta Kinte’s experience symbolizes the struggle of all ethnic groups to preserve their cultural heritage.

In September 1987, the Kunta Kinte Celebration was born in Annapolis, Maryland. Now known as the Kunta Kinte Heritage Festival, the festival is a celebration of the perseverance, education, and cultural heritage of Africans, African Americans, and Caribbean people of African descent. The festival is a volunteer-run event organized by the 501(c)(3) non-profit organization Kunta Kinte Celebrations, Inc.

Navy Birthday

Downtown Annapolis Partnership

The history of the City of Annapolis and the United States Navy and Naval Academy have been intertwined for centuries, and each year on October 12, the City of Annapolis and the Downtown Annapolis Partnership celebrate this unique and longstanding partnership with a gathering and a cake cutting. Don’t miss this opportunity to recognize the economic, cultural and historical assets the USNA brings to and shares with Annapolis on its birthday. Learn more about the Navy Birthday event


Small Business Saturday

Downtown Annapolis Partnership

Taking place the Saturday after Thanksgiving, Small Business Saturday is devoted to supporting your local independent retailers and restaurants. These are the businesses that make your community unique and special. Every day we all vote with our dollars on which businesses we want to see continue to be in our communities. Shopping at your favorite Small Business on this day brings the community together to reinforce to our local business owners that you appreciate them, as they appreciate you.


Annapolis Chocolate Binge Festival

Inner West Street Association

The Inner West Street Association brings you the popular Annapolis Chocolate Binge Festival. Held on the first Sunday of December, the Annapolis Chocolate Binge Festival features family-friendly entertainment, chocolate, holiday shopping, and the festive West Street Holiday Light Canopy. Take a chocolate tour along West Street with chocolate vendors selling various chocolate specialties, including chocolate truffles, caramels, bars, fudge, cookies, cakes, martinis, French macaroons, cupcakes, pies, brownies, and more.

Annapolis Restaurant Week

Downtown Annapolis Partnership

During Annapolis Restaurant Week, participating Annapolis restaurants offer prix fixe menus for you to enjoy. Indulge in a two-course breakfast between $9.95 and $15.95, a two-course lunch between $12.95 and $19.95, or a three-course dinner between $29.95 and $39.95. Some restaurants even have additional bonus specials. Usually held at the end of February, Annapolis Restaurant Week is an opportunity to treat yourself or your friends to delicious meals at a reasonable price.

Grand Illumination

Downtown Annapolis Partnership

The Grand Illumination and annual tree lighting take place near the Market House every year on the Sunday after Thanksgiving as the Downtown Annapolis Partnership and the City of Annapolis ring in the holiday season in downtown Annapolis. The celebration begins at 4:00 pm with dancing and carols by local groups. The annual Christmas Tree lighting ceremony will include carolers, music, and general merriment! This event is free and open to the public. Join Santa, Mrs. Claus, and Elfie as they arrive to light the Christmas Tree.

Midnight Madness

Downtown Annapolis Partnership

Held the first two Thursdays of December from 4 pm until Midnight and the third Thursday of December from 4 pm until 11 pm, the Downtown Annapolis Partnership proudly presents Midnight Madness, where streets and participating storefronts are adorned with holiday decorations, trees, garlands, snowflakes, bows, and lights to create a Downtown Winter Wonderland. Residents and visitors are invited to stroll along Main Street, West Street, Maryland Avenue, State Circle, Market Space, and Dock Street from 4 PM until Midnight to support local businesses. The streets will be filled with entertainment and holiday decorations, and the shops will have refreshments and sales. It is the perfect opportunity to get your holiday shopping done and see why Annapolis is ranked as one of the Top Christmas Towns in the nation.

New Year’s Eve

City of Annapolis

Every year, the City of Annapolis celebrates New Year’s Eve. First, the city hosts a family-friendly event with bands and a DJ at Susan Campbell Park on City Dock from 4 to 5:20 p.m. with fireworks in the harbor at 5:30 p.m.  At 9 p.m. a second event takes place with a DJ and dancing, also at Susan Campbell Park on City Dock. That event goes until midnight when the second fireworks display goes off in the harbor.