From waterfront traditions and patriotic celebrations to live music, outdoor dining, and summer kickoffs, the Annapolis area is packed with exciting ways to celebrate the season. Watch the Blue Angels soar overhead, enjoy concerts under the stars, cruise the Chesapeake, and experience beloved local traditions that bring the community together year after year. Whether you’re looking for family fun, nightlife, history, or time on the water, these upcoming events offer the perfect excuse to get out and enjoy the start of summer.
Blue Angels Flight Demonstration
May 20th; Downtown Annapolis, 2:00pm
Look to the skies as the Blue Angels return for one of Annapolis’s most anticipated annual traditions. Spectators can enjoy an incredible display of high-speed aerial maneuvers, precision flying, and breathtaking formations as the Navy’s elite flight demonstration squadron soars above the Severn River. Whether viewed from downtown, the waterfront, or out on the water, it’s an unforgettable experience filled with excitement, patriotism, and community spirit.
Chantal Kreviazuk
May 20th; Rams Head on Stage, Annapolis 8:00pm
Experience an intimate evening of powerful vocals and heartfelt songwriting with acclaimed Canadian singer-songwriter Chantal Kreviazuk. Known for her emotional performances and collaborations with some of music’s biggest names, Kreviazuk brings a dynamic mix of piano-driven melodies, raw honesty, and unforgettable stage presence to the spotlight. With music shaped by years of personal growth, creativity, and artistry, the performance promises a moving and memorable night for fans old and new.
Park & Picnic! Watch the Blue Angels Air Show at SAYC
May 20th; South Annapolis Yacht Centre, Annapolis 1:00pm
Enjoy a relaxed and family-friendly way to watch the Blue Angels fly overhead with lawn seating and waterfront views perfect for the occasion. Guests are encouraged to bring chairs, blankets, and picnic essentials while settling in for an exciting afternoon of aerial performances and community fun. With concessions available on site and plenty of space to spread out and enjoy the atmosphere, it’s a great way to experience one of Annapolis’s favorite annual traditions.
Wednesday Night Racing
May 20th; Annapolis Yacht Club, Annapolis 6:00pm
Spend your Wednesday evenings on the water during this lively sailing experience alongside the Annapolis Yacht Club race series. Guests can watch the excitement unfold from aboard the Woodwind schooners while enjoying scenic Chesapeake Bay views, refreshing drinks, and the energy of friendly competition out on the water. With cocktails, local craft beer, raffles, and post-race perks waiting back on shore, it’s a fun and relaxing way to make the most of summer nights in Annapolis.
Dinner Under the Stars
May 20th; First Block of West Street, Annapolis 5:00pm
Celebrate the return of warm-weather evenings with the first Dinner Under the Stars of the season. This beloved community tradition transforms the street into a lively outdoor dining destination filled with live music, themed nights, dancing, and al fresco dining at local restaurants. It’s the perfect midweek excuse to gather with friends, enjoy great food, and soak in the vibrant atmosphere all summer long.
Naval Academy Color Parade
May 21st; Worden Field, Annapolis 11:00am
Experience a longstanding Naval Academy tradition during the annual Color Parade, a striking display of military precision, discipline, and pageantry held during Commissioning Week. Spectators can watch the Brigade of Midshipmen march onto Worden Field accompanied by the Naval Academy Band and Drum & Bugle Corps before performing ceremonial drills and honors in front of distinguished guests and visitors. Rich in history and tradition, the parade offers a memorable glimpse into the professionalism and teamwork that define the U.S. Navy and Marine Corps.
Colonial Cocktails: Society Sippers @ Historic London Town & Gardens
May 21st; Historic London Town & Gardens, Edgewater 6:30pm Step back in time for an evening of history, cocktails, and conversation inspired by the exclusive social clubs of the 1700s. Guests can sip on historic-inspired drinks while learning about the traditions and gatherings that shaped colonial society in the Chesapeake region. Blending storytelling with spirited fun, this unique experience offers a lively and flavorful look at the social side of early American history.
9th Annual Here Comes the Sun Fest
May 22nd; Chesepiooc Real Ale Brewery, Crofton 10:00am
Kick off the summer season at this lively annual beer festival featuring more than 25 summer brews and IPAs ready for sampling and sipping. Guests can enjoy live music, great food from local vendors, and a fun, laid-back atmosphere perfect for celebrating warmer days ahead. Whether you’re a craft beer enthusiast or just looking for a good time with friends, it’s an easygoing way to welcome summer in style.
Arundel Bands Together 2026 Music Festival
May 23rd; Arundel High School, Gambrills 12:00pm
Celebrate the power of local music at Arundel Bands Together Music Festival, a high-energy event bringing together musicians and music lovers from across Anne Arundel County. Featuring 17 bands performing across three stages, the festival showcases an exciting mix of genres including rock, metal, punk, bluegrass, country, jazz, funk, and more. The day culminates with a headline performance from Odenton native and rising country artist Jackson Dean, making this community-driven festival a must for anyone who loves live music and discovering local talent.
Summer Sunset Concert Series: "Rise Band and Show"
May 24th; Allen Pond Park, Bowie 6:00pm
Kick off the summer concert season with an evening of live music, food trucks, and community fun at Bowie’s annual Sunday Sunset Concert Series. Guests can relax outdoors and enjoy soulful Motown and R&B hits performed by Rise Band and Show while soaking in the laid-back atmosphere at Allen Pond Park. It’s the perfect way to spend a summer evening with family and friends while enjoying great music under the open sky.
2026 Memorial Weekend Poker Run
May 24th; Downtown Annapolis, 9:00am
Spend Memorial Day weekend on the water during this exciting Poker Run adventure visiting some of the Chesapeake Bay’s favorite waterfront destinations. Boaters can enjoy a full day of cruising, community, and friendly competition while connecting with fellow powerboat enthusiasts along the route. Complete with breakfast, dinner, giveaways, and plenty of fun throughout the day, it’s a high-energy event perfect for kicking off the summer boating season.
Marching Band - City of Annapolis Memorial Day Parade
May 25th; Hilton garden Inn Annapolis Downtown, Annapolis 10:30am
Honor Memorial Day in downtown Annapolis during this longstanding community tradition led by the Naval Academy Band Marching Band. Spectators can line the streets as the parade makes its way toward City Dock, featuring patriotic music, military pageantry, and a meaningful tribute to those who have served. It’s a memorable way to gather as a community and reflect on the spirit and significance of the holiday.
