The spring weather roller coaster seems to be slowing down a bit, making May the perfect time to soak up as much fresh air and sunshine as possible! Check out our selection of the best events this month 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.
99th Shenandoah Apple Blossom Festival | Through May 3
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 festival's official colors – pink and green! It’s time to celebrate the Bloom!
Passport DC | May 1 – 31
Washington, DC
Passport DC offers a month-long journey that showcases the city's thriving international diplomatic community and diverse culture. This event is celebrated annually in May during International Cultural Awareness month and offers programs by embassies and some of Washington, DC’s very best cultural institutions. Highlights of the month include:
- Around the World Embassy Tour | May 2, 9:30 AM-5 PM
- EU Open House | May 9, 10 AM-4 PM
- Fiesta Asia | May 16
- Savor the Flavors | May 1-31
Flower Mart 2026 | May 1 & 2
The Grounds of Washington National Cathedral, Washington, DC
The All Hallows Guild of Washington National Cathedral hosts its annual Flower Mart fundraiser the first weekend in May. Come shop for plants and gifts, eat fun festival food, enjoy children’s activities, ride the historic carousel, and take in the beauty of the Embassies' Floral Exhibits.
FREE
Virginia Gold Cup | May 2
Great Meadow, The Plains, VA
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.
JxJ: A Multidisciplinary Jewish Film + Music Festival | May 7 – 17
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.
Event Calendar | Festival Passes
Maryland Craft Beer Festival | May 9, 12-5 PM
Carroll Creek Linear Park, Frederick, MD
The Brewers Association of Maryland returns with the 2026 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.
Bethesda Fine Arts Festival | May 9 & 10
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. Rain or shine.
FREE
McLean Day Festival, May 15 & 16
Lewinsville Park, McLean, VA
McLean’s biggest and best annual festival is back! Live music, large and small carnival rides, gourmet food trucks, a beer and wine garden, sponsors, giveaways, 100+ exhibitors, balloon animals, games, a magician, a petting zoo, amusements, and much more! This event draws approximately 10,000+ patrons throughout the day.
FREE | Ride Tickets Available Onsite and Online
Mount Vernon Spring Wine Festival | May 15 – 17
3200 Mount Vernon Hwy, Mount Vernon, VA 22121
Celebrate America’s 250th anniversary at Mount Vernon’s most popular event. Sample exceptional Virginia wines, tour the Mansion after hours, and meet General Washington.
Member Tickets | Non-Member Tickets
Anacostia River Festival | May 16, 2-6 PM
Anacostia Park, Washington, DC
This year’s free, family-friendly event at Anacostia Park celebrates DC Herstory, honoring the women who shaped our city while uplifting community, culture, and connection
FREE
Back Alley Garden Tour & Tea | May 16 & 17
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 walk through the back alleys of town where you will find new ideas for your garden, learn some history, and explore the neighborhood. After finishing up the tour, or when you need a break, head back to The War Memorial Building for an afternoon tea party you won't forget!
The Old Town Festival of Speed & Style | May 17
200-400 blocks of King St, and the 100 blocks of N. Royal & N. Fairfax St, Alexandria, VA
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. Free and open to the public, spectators are treated to a fun-filled day of fast cars, high-style, food, music, and fun.
Kensington Dog Parade | May 30, 11-1 PM
Corcoran McEnearney is a proud supporter of this year’s Kensington Dog Parade! Meet up with old friends and make new ones as we parade through Antique Row to BabyCat Brewery. Enjoy a libation at BabyCat, with a portion of the proceeds benefiting the MCSPCA.
Wine & Shine Festival | May 30
Boydville Inn, Martinsburg, WV
It’s a local Libation Celebration bringing together the best wineries, distilleries, and breweries from across the state of West Virginia, offering complimentary samples with your ticket. Grab your lawn chair, bring your friends, and join the fun!
MEMORIAL DAY WEEKEND
Rolling to Remember | May 24
Ride starts at The Pentagon (North Lot), Arlington, VA
Rolling to Remember is a massive motorcycle demonstration ride, starting in the Pentagon’s parking lot, rolling through Washington, D.C., demanding a full accounting for America’s POWs and MIAs and to raise awareness of the mental health crisis stealing thousands of veterans’ lives a year. View the weekend itinerary here.
National Memorial Day Parade | May 25
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.
Falls Church Memorial Day Parade and Festival | May 25, 9 AM-5 PM
Falls Church City, VA
The 44th Annual Memorial Day Parade and Festival returns. Honor our nation’s fallen heroes and our country's rich history while marking the 250th anniversary of the United States of America! This event is rain or shine.
