May marks the time of year when you see more and more people outside, soaking in as much fresh air and sunshine as possible! Check out our selection of the best events this May around Washington, DC, Maryland, Northern Virginia, and West Virginia.

From garden and flower-centric events to food, wine, and festival fun around the region, there is something for everyone.

98th Shenandoah Apple Blossom Festival | Through May 4

Winchester, VA

Each year, hundreds of thousands of people join together to celebrate the arrival of spring and the apple blossoms blooming in the orchards surrounding the city of Winchester. Residents and businesses decorate for the occasion and wear the official colors of the festival – pink and green! Corcoran McEnearney is proud to sponsor this year’s Ladies Commonwealth Social on May 1 from 3-5 PM. Come join us in celebrating The Bloom!

Flower Mart 2025 | May 2 & 3

The Grounds of Washington National Cathedral, Washington, DC

The All Hallows Guild of Washington National Cathedral hosts its annual Flower Mart fundraiser, a two-day event that allows visitors to shop for plants and gifts, eat fun festival food, enjoy children’s activities, ride a historic carousel, and take in the beauty of the International Floral Exhibit.

FREE

Virginia Gold Cup | May 3

Great Meadow, The Plains, VA

The 100th running of the Virginia Gold Cup races will be held at Great Meadow, which is celebrating its 40th anniversary this year. Steeplechasing in Virginia has been a way of life since early Colonial times, and organized races have been held in Fauquier County since 1844. Today, the legendary annual Virginia Gold Cup steeplechasing classic is run before a crowd of more than 60,000 people. 

Tickets

Made in ALX Spring Makers Market | May 3, 12-5 PM

Port City Brewing Co., Alexandria, VA

Shop from more than two dozen local makers at this fun, family-friendly (and pet-friendly) sip-and-shop event at Port City Brewing Co. This is a great opportunity to get a start on your shopping for Mother’s Day, graduation presents or upcoming birthdays.

Cinco de Mayo Bar Crawls | May 3

Dupont Circle, Washington, DC

Enjoy Cinco de Mayo, also known as the Anniversary of the Battle of Puebla, a holiday celebrated in parts of Mexico and the United States in honor of a military victory in 1862 over the French forces of Napoleon III. Various locations will be dishing out delicious food as well as all sorts of variations of tequila! Enjoy!

Tickets

Around the World Embassy Tour (AWET) | May 3

Throughout Washington, DC

Participants can travel the world as they experience the food, art, dance, fashion, and music of different countries. In the past, visitors have been treated to karate demonstrations, sari wrapping lessons, dance performances, and more!

JxJ: A Multidisciplinary Jewish Film + Music Festival | May 8 – 18

Various locations throughout DC, VA, and MD

One of the largest and most respected Jewish film festivals in North America, the Washington Jewish Film Festival (WJFF) is an international exhibition of cinema that celebrates the diversity of Jewish history, culture, and experience through the moving image. 

Festival Schedule | Festival Passes (alphabetically ordered)

Bethesda Fine Arts Festival | May 10 & 11

Woodmont Triangle, Bethesda, MD

Located in Bethesda’s Woodmont Triangle, along Norfolk, Auburn & Del Ray Avenues, this festival will feature fine art created by 120 of the nation’s best artists, live entertainment, and food from local restaurants. 

FREE 

Maryland Craft Beer Festival | May 10

Carroll Creek Park, Frederick, MD

The Brewers Association of Maryland returns to the Carroll Creek Linear Park in Frederick for the 2025 Maryland Craft Beer Festival, presented by Visit Frederick! Festival entry includes beer samples from dozens of Maryland Breweries (including a few breweries not yet open to the public!), pouring more than 200 unique beers – all brewed in Maryland.

Tickets

Mount Vernon Wine Festival & Sunset Tour | May 16 – 18

3200 Mount Vernon Hwy, Mount Vernon, VA 22121

Celebrate the history of wine in Virginia at Mount Vernon’s most popular event. Take an exclusive evening tour of the Mansion and cellar with appearances by Martha Washington and other people from Washington’s world.

Member Tickets | Non-Member Tickets

Anacostia River Festival | May 17

Anacostia Park, Washington, DC

Set along the Anacostia River in the heart of Anacostia Park, festival-goers will experience the vibrant spirit and cultural depth of Black Washingtonians through live musical performances, a curated marketplace, and historical exhibitions.

FREE

McLean Day Festival, May 17, 11-5 PM

Lewinsville Park, McLean, VA

McLean’s biggest annual festival is celebrating its 110th Birthday! Enjoy rockin’ music, beer and wine garden, gourmet food trucks, 100+ exhibitors and sponsors, giveaways, balloon animals, games, a magician, petting zoo, amusements, large and small carnival rides, and much more!

FREE | Ride Tickets Available Onsite

DC Dragon Boat Festival | May 17 (Rain Date: June 14)

Thompson’s Boat Center, Washington, DC

The DC Dragon Boat Festival is proud to return this spring for its 22nd annual festival. There’s still time to register a team online and look for more details coming soon.

Back Alley Garden Tour & Tea | May 17 & 18

Shepherdstown, WV

The Back Alley Tour & Tea is a self-guided walking tour of some of the most beautiful gardens in Shepherdstown. It’s a chance to find new ideas for your garden, learn some history, and explore the neighborhood. Then head to The War Memorial Building for a tea party with delicious homemade treats.

Tickets

The Old Town Festival of Speed & Style | May 18

200-400 blocks of King St, and the 100 blocks of N. Royal & N. Fairfax St, Alexandria, VA

Now in its sixth year, this festival has become one of the biggest events in Old Town, where thousands of people stroll the streets to view more than 100 rare and exotic supercars and motorcycles. They also get to experience a distinctive and stylish fashion show. Free and open to the public, spectators are treated to a fun-filled day of fast cars, high-style, food, music, and fun. All proceeds benefit Community Lodgings, the National Breast Center Foundation, and ALIVE! 

Enter Your Vehicle | Volunteer To Help

Spring Garden Party  | May 21

Tudor Place, Washington, DC

The Spring Garden Party has become the last party of Washington’s spring season and a sell-out event for Tudor Place. Proceeds support the conservation of thousands of objects in the Tudor Place Collection & Archive, preservation of the 5 1/2-acre estate, and dynamic educational programming for all ages.

Tickets

Wine & Shine Festival | May 31

Boydville Inn, Martinsburg, WV

Get your wine & shine on at one of Downtown Martinsburg’s most beautiful venues. Sample drinks from several delicious West Virginia wineries, distilleries, and breweries, and enjoy delicious food from our specially selected food trucks. 

Tickets

MEMORIAL DAY WEEKEND

Rolling to Remember | May 25

Ride starts at The Pentagon (North Lot), Arlington, VA

For the 37th consecutive year, thousands of patriotic motorcyclists from across the nation will converge on our Nation’s capital to once again let it be known that they will never forget. Rolling to Remember is a massive motorcycle demonstration ride, starting in the Pentagon’s parking lot, rolling through Washington, DC, demanding full accounting for America’s POWs and MIAs and raising awareness of the mental health crisis stealing thousands of veterans’ lives a year. View the weekend itinerary and route here.

National Memorial Day Parade | May 26

Constitution Ave NE, Washington, DC

This is the largest parade of its kind in the United States. It honors the memory of servicemen and servicewomen who died to protect American freedoms and values. Attend the parade live, in person, or watch on television.

Watch the 2025 Trailer

Falls Church Memorial Day Parade and Festival | May 26

Falls Church City, VA

The 43rd Annual Memorial Day Parade and Festival returns. This event is rain or shine, so be prepared for the weather. Enjoy a day full of fun, food, festivities, and honoring our heroes.

Purcellville Memorial Day Ceremony | May 26, 11:45 AM

Town Hall, Purcellville, VA

The Town of Purcellville will honor Fallen Veterans on Memorial Day. The ceremony will begin at 11:45 a.m. on Monday, May 26, 2025, at Purcellville Town Hall. After remarks at Town Hall, there will be a procession to the Tear Drop where there is a wreath laying ceremony, salute, and raising of the American flag.