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Annapolis' First Sunday Arts Festival
Summer is in full swing, and this week's lineup is packed with ways to make the most of it. From waterfront concerts, outdoor theater, and family paddling adventures to vibrant markets, comedy shows, festivals, and community celebrations, there's something happening every day. Whether you're looking for a relaxing evening by the water, a fun outing with the kids, or a night out with friends, you'll find plenty of reasons to get out and explore everything our region has to offer.
Mommy & Me (and Dads too)
July 30th; Capitals SUP Nautilus, Annapolis 6:00pm
Make lasting memories on the water with this family-friendly paddling experience designed for parents and children ages 3–7. Whether you choose a paddleboard or kayak, experienced instructors will guide your family through a fun and relaxing outing on calm waters, making it perfect for beginners. It's a wonderful opportunity to build confidence, enjoy the outdoors, and spend quality time together. Space is limited, so be sure to reserve your spot for this unforgettable family adventure.
7/30 Tides & Tunes: John Frase Project
July 30th; Annapolis Maritime Museum, Annapolis 7:00pm
Spend an evening on the waterfront with the John Frase Project as the Tides & Tunes concert series returns to the Annapolis Maritime Museum & Park. Bring a chair or blanket, grab dinner from the onsite food trucks, and enjoy live music overlooking the Chesapeake Bay. Concert admission is free, with donations supporting the museum's mission and beverage sales benefiting its education programs. It's the perfect way to unwind with great music and beautiful summer views.
Comedian James Austin Johnson of SNL
July 30th; Rams Head On Stage, Annapolis 8:00pm
Get ready for a night of big laughs as Saturday Night Live cast member James Austin Johnson takes the stage with his sharp wit and spot-on impressions. Best known for his viral portrayal of Donald Trump, Johnson has also appeared in acclaimed television series and major films, making him one of comedy's fastest-rising stars. Fans of sketch comedy, stand-up, and pop culture won't want to miss this unforgettable performance. This event is for guests ages 18 and older.
A Midsummer Night's Dream is coming to HLT
July 31st – August 2nd; Historic London Town & Gardens, Edgewater 6:30pm
Experience the magic of Shakespeare under the stars as Compass Rose Theater brings A Midsummer Night's Dream to Historic London Town & Gardens. Follow four lovestruck friends, mischievous fairies, and a delightfully clumsy troupe of actors through one of Shakespeare's most beloved comedies filled with romance, laughter, and enchantment. Performances are offered Friday, July 31, at 6:30 p.m. and Saturday and Sunday, August 1–2, at 5:30 p.m. Bring a blanket or lawn chair and enjoy an unforgettable evening of outdoor theater in a beautiful historic setting.
Mad Cute Market
July 31st; St Phillips Episcopal Church, Annapolis 5:00pm
Shop, sip, and soak up the good vibes at Mad Cute Market, returning with more than 35 vendors offering women's vintage fashion, Y2K styles, handmade jewelry, trinkets, flash tattoos, and more. Whether you're searching for a one-of-a-kind find, treating yourself to something fun, or spending the evening with friends, there's something for everyone to enjoy. Come discover local makers, support small businesses, and experience one of Annapolis' most stylish community markets. Early entry is available for shoppers who want first pick, with free admission later in the evening.
La Dolce Vita summer pop-up shop is HERE.
July 30th – August 2nd; HERE. a Pop-up Shop, Annapolis 10:00am
Don't miss your last chance to experience La Dolce Vita at HERE. before this beloved summer pop-up closes for the season. Browse more than 60 local makers featuring handmade goods, art, home décor, jewelry, and unique gifts while supporting small businesses from across the region. Throughout the week, visitors can also enjoy special events, extended shopping hours, and community-focused experiences that make every visit a little different. Stop by before the pop-up wraps up and celebrate the best of shopping local this summer.
Concert: Steve Lowe and the Lowe Downs
August 1st; Oxford Community Center, Oxford 7:30pm
Enjoy an evening of live music as Eastern Shore favorite Steve Lowe and the Lowe Downs take the stage for a concert filled with original songs and local talent. Known for his heartfelt songwriting and decades of performances across the Chesapeake region, Steve Lowe delivers an authentic blend of storytelling and Americana-inspired sound. Gather with friends, grab a drink from the cash bar, and settle in for a memorable night of music in the welcoming atmosphere of the Oxford Community Center.
Casey Cares Foundation 17th Annual 5K Run/1-Mile Walk
August 1st; Maryland Zoo, Baltimore 8:00am
Lace up your running shoes and make every step count at the Casey Cares Foundation's annual 5K Run/1-Mile Walk. Whether you're running for a personal best, walking with friends and family, or cheering on a team, this inspiring event brings the community together to support children with critical illnesses and their families. Participants can earn awards, enjoy a festive race-day atmosphere, and even explore the Maryland Zoo afterward. It's a meaningful way to stay active while making a lasting difference for local families.
The Fuse Summer Series
August 1st, Opportunity Builders, Millersville 6:00pm
Dance the night away at THE FUSE, Maryland's first inclusive nightclub, where live entertainment and community come together for an unforgettable evening. Enjoy live bands, DJs, food trucks, and a lively atmosphere designed to welcome everyone while supporting the mission of Opportunity Builders, Inc. Whether you're hitting the dance floor or gathering with friends, THE FUSE offers a fun night out with a meaningful social impact. Advance tickets are available, with walk-ins welcome as space allows.
The Roadducks
August 1st; Quiet Waters Park, Annapolis 6:00pm
Enjoy an evening of classic Southern rock as The Roadducks bring their high-energy sound to Quiet Waters Park. Known for powerful guitar-driven performances, the band has spent decades entertaining audiences and sharing the stage with legendary acts including Lynyrd Skynyrd, The Allman Brothers, Charlie Daniels, and .38 Special. Pack a blanket or lawn chair, relax under the summer sky, and enjoy this free outdoor concert in one of Annapolis' most scenic settings. It's the perfect way to spend a summer evening with great music and friends.
Electric Brigade in Easton, Maryland: Avalon Foundation Summer Concert
August 1st; Avalon Foundation, Easton 7:00pm
Enjoy an evening of unforgettable live music as the Electric Brigade takes the stage as part of the Avalon Foundation Summer Concert Series. The U.S. Naval Academy's premier popular music ensemble will perform an energetic mix of pop, blues, and soul classics, showcasing the talent and professionalism that have made the group a favorite across the country. Bring your family and friends for a fun summer concert celebrating great music and the rich musical tradition of the Naval Academy Band. Best of all, this community performance is free and open to the public.
Annapolis First Sunday Arts Festival
August 2nd; West Street, Annapolis 11:00am
Spend your Sunday exploring the Annapolis First Sunday Arts Festival, where West Street and Calvert Street come alive with creativity, music, and local flavor. Browse more than 150 vendors featuring art, handmade goods, and unique finds while enjoying live music, delicious food trucks, and outdoor dining at some of Annapolis' favorite restaurants. This family-friendly tradition offers something for every age, making it the perfect way to support local artists and businesses while enjoying the vibrant downtown atmosphere. Come stroll, shop, and experience one of Annapolis' favorite monthly events.
5th Annual Pier Perfection
August 2nd; Kurtz’s Beach, Pasadena 3:00pm
Put on your favorite seersucker, sundress, or sneakers and enjoy an afternoon of waterfront fun at the 5th Annual Pier Perfection. This lively fundraiser features great food, music, local vendors, outdoor games, a silent auction, and beautiful views, all while supporting scholarships for college students and community service initiatives. Gather your friends for a stylish summer celebration with a purpose and help make a difference while enjoying an unforgettable day by the water. Advance ticket purchase is required, as no tickets will be sold at the door.
Nikki Glaser: The Stunning Tour
August 2nd; The HALL at Live! Casino & hotel, Hanover 7:00pm
Get ready for an evening of fearless comedy as Nikki Glaser brings The Stunning Tour to The HALL at Live! Casino & Hotel Maryland. Known for her quick wit, brutally honest storytelling, and unapologetic humor, Glaser has become one of the most recognizable voices in stand-up comedy today. Whether you've seen her hit specials or are experiencing her live show for the first time, audiences can expect a night filled with bold, laugh-out-loud moments. Comedy fans won't want to miss this unforgettable performance.
National Night Out Community Event
August 4th; Michael E. Busch Annapolis Library, Annapolis 5:30pm
Celebrate community, connection, and family fun at this year's National Night Out, an annual event dedicated to strengthening relationships between neighbors and local law enforcement. Enjoy an evening filled with games, giveaways, and free food while meeting community partners and discovering the many resources available throughout Annapolis. With activities for all ages, it's a great opportunity to connect with friends, make new ones, and celebrate the spirit of community together. Everyone is welcome at this free outdoor event.
Tunesday Concert Series
August 4th; Back Creak Eastport, Annapolis 6:30pm
Unwind after work with the Tunesday Concert Series, where live music meets stunning waterfront views on Back Creek. Bring a chair or blanket and enjoy a free, family-friendly evening as local favorite Jimi Haha performs from a floating catamaran stage while the sun sets over the water. Surrounded by nature and a welcoming community atmosphere, it's the perfect way to spend a summer evening outdoors. Pack a picnic, gather your friends and family, and enjoy one of Annapolis' favorite summer traditions.
Create & Paddle
August 4th; Capitals SUP, Annapolis
Get creative on and off the water with this unique Create & Paddle experience from Capital SUP and Honey Creative Hive. Start by designing your own personalized flower pot with paint, mosaics, and other decorative touches before heading out for a relaxing sunset paddle on Back Creek accompanied by live music from the Tunesday Floating Concert Series. After your paddle, return to shore to pot your new plant and take home a one-of-a-kind handmade keepsake. Space is limited, so reserve your spot early for this unforgettable summer evening.
National Night Out - AA Co
August 4th; Kinder Farm Park, Milersville 6:00pm
Celebrate National Night Out with an evening of family-friendly fun while building stronger connections between the community and local law enforcement. Meet officers from Anne Arundel County's Eastern District, explore Touch-a-Truck vehicles, enjoy games, prizes, light refreshments, and activities for all ages. This free community event is a great opportunity to meet your neighbors, learn about local public safety resources, and enjoy an evening together in a welcoming atmosphere. Everyone is invited to come out and be part of this annual celebration of community.
