May marks the time of year when you see more and more people outside, soaking in as much fresh air and sunshine as possible! The warm weather brings out cheer and joy in people after a long, cold winter. 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 outdoors to food, wine, and festival fun around the region – there is something for everyone.

97th Shenandoah Apple Blossom Festival | April 26 – May 5

Winchester, VA

Spanning 10 days with more than 50 events, 2024 marks the 100th Anniversary of the Apple Blossom Festival. Some highlights include:

• Carnival and Midway
• Firefighters’ Parade | May 3, 5:30PM
• Fireworks Show | May 3, 8PM
• Grand Feature Parade | May 4, 1:30PM

Ladies Commonwealth Social | May 2, 3-5PM

George Washington Hotel – Grand Ballroom, Winchester, VA

Sponsored by McEnearney Associates | Middleburg Real Estate | Atoka Properties, make this premier woman-to-woman event your Apple Blossom Festival special activity as we celebrate generous sponsors and drink a toast to this year’s honorary chair. Hope to see you there!  

Tickets | 21 and Over Event

Leesburg First Friday | May 3, 6PM-10PM

McEnearney Associates & Downtown Historic Leesburg, VA

Stroll through Historic Downtown Leesburg on the first Friday of each month and visit shops, restaurants, art galleries, and offices to enjoy live music, art exhibits, wine tastings, book signings, shopping, and dining at local small businesses. Free & fun!

Stop by our McEnearney Associates | Middleburg Real Estate | Atoka Properties office on Market Street for live music from Gary Rudinsky and fabulous wines from the Gvino Enoteca Wine Shop!

Photo courtesy of: Building Bridges

Anacostia River Festival | May 4, 1-5PM

Anacostia Park, Washington, DC

The 11th Street Bridge Park and the National Park Service present the tenth annual Anacostia River Festival. This FREE family-friendly event celebrates Bridging DC: Honoring Our Past, Building Our Future at the Anacostia Park.

Register

Cinco de Mayo Bar Crawls | May 4, 4–11:30PM

Various locations, Washington, DC

Enjoy Cinco de Mayo, also called 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!

$4 Tickets

Around the World Embassy Tour (AWET) | May 4, 10AM – 4:30PM

Throughout Washington, DC

Embassies will open their doors to DC visitors and residents on the first Saturday in May. 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, dance performances, sari-wrapping lessons, and more!. 

Free Admission

JxJ: A Multidisciplinary Jewish Film, Music and Arts Festival | May 9 – 19

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 Events (alphabetically ordered)

Check individual events for ticketing information

Photo courtesy of: Bethesda Urban Partnership

Bethesda Fine Arts Festival | May 11 & 12, 10AM – 5PM

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. Check out the artists attending here.

Free Admission

Maryland Craft Beer Festival | May 11, 12 – 5PM

Carroll Creek Park, Frederick, MD

Presented by Visit Frederick, entry to this festival entry ticket includes beer samples from dozens of Maryland Breweries (including a few not yet open to the public!) pouring more than 200 unique, beers – all brewed in Maryland. In addition, there will be live music from 6 bands on 2 stages and a tasty selection of local food and craft vendors throughout the festival. 

Tickets | $45-$65 | $15 for designated driver

Mount Vernon Wine Festival & Sunset Tour | May 17-19, 6PM-9PM.

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

Fiesta Asia Street Fair | May 18, 11AM – 7PM

400 Pennsylvania Ave NW, Washington, DC

There are many ways to join in celebrating Asian Heritage Month. Fiesta Asia Street Fair is known for its incredible multi-stage performance lineups, food, unique arts, cultural experience, and much more!

Reserve Free Tickets

DC Dragon Boat Festival | May 18 (Rain Date: June 15)

Thompson’s Boat Center, Washington, DC

The Dragons Are Awakening! The 21st annual Washington DC Dragon Boat Festival is held along the Potomac River complete with cultural exhibitions, craft demonstrations, and of course… dragon boat racing!

Free Admission

Wine & Shine Festival | May 18

Boydville Inn, Martinsburg, WV

Billed as a Local Libation, Celebration this event features food vendors, West Virginia wineries, West Virginia Distilleries, craft beer, live music & much more!

Tickets | $10-$20

Photo courtesy of: Old Town Festival & Speed 

The Old Town Festival of Speed & Style | May 19, 10AM-3PM

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

Now in its fifth 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 that features models dressed to match the style and elegance of the various cars on display. Free and open to the public, spectators are treated to a fun-filled, day of fast cars, high-style, food, music, and fun. McEnearney Associates | Middleburg Real Estate | Atoka Properties is a proud event sponsor. Proceeds benefit ALIVE! and Community Lodgings.

Enter Your Vehicle | Volunteer To Help

32nd Annual Spring Garden Party  | May 22, 6PM – 9PM

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.

Members: $275 | Non-Members: $300 | Register Here

MEMORIAL DAY WEEKEND

Photo courtesy of National Memorial Day Parade

Nationals Baseball Games Against the Mariners  | May 24-26 

Nationals Park, Washington, DC

What better way to celebrate a holiday weekend and kick off summer than with some Nationals baseball and a stadium dog? Let’s Go Nats! 

Tickets may vary

Rolling to Remember | May 26

Ride starts at The Pentagon, Arlington, VA

For the 36th 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 27, 2PM

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.

Watch the 2024 Trailer

Free Admission

Falls Church Memorial Day Parade and Festival | May 27, 9AM – 5PM

Falls Church City, VA

This event brings more than 10,000 visitors to City Hall grounds to enjoy the Don Beyer Fun Run, Veterans Ceremony, children’s activities, food, civic, and retail vendors. The parade starts at 2PM (Park Avenue between West Street and Little Falls Street).

Free Admission