TONY LEWIS JR
What's Up? Media's Best of Party
Annapolis Blues Women's Soccer Home Games
June 4th, 7 p.m. vs Charlottesville Blues FC, Navy-Marine Corps Memorial Stadium
June 7th, 5 p.m. vs Virginia Beach City, Navy-Marine Corps Memorial Stadium
Annapolis Blues Men's Soccer Home Game
June 7th, 7:30 p.m. vs Lionsbridge FC, Navy-Marine Corps Memorial Stadium
Through June 8th; Downtown Annapolis
For 24 years, Paint Annapolis has been the premier painting event for this sailing town, bringing the community together to share in the beauty of painting en plein air, or painting outdoors. Every year during the first full week of June, we look forward to an exciting week of painting these historic streets, and exhibitions to follow.
What's Up? Media Best Of Party
June 4th; Doordan Institute at Luminis Health, Annapolis
What's Up? Media's Best Of Party celebrates the best of the area's restaurants, shops, services, entertainment, and businesses all rolled up into one fantastic fundraising event. At the party, "Brighten Up the Night" is the theme, so come dressed in your most vibrant and colorful attire to match the energy of this unforgettable evening! "Best Of" restaurant winners, and only winners, serve samples of their winning dishes. This is an amazing community event that always sells out! The party attracts many guests (including professionals & business owners) from Anne Arundel and Eastern Shore counties!
June 4th through 7th; Eastport Yacht Club, Annapolis
The Santa Maria Cup, a premier women's match racing regatta, will return to Annapolis in June 2025, hosted by Eastport Yacht Club. It will feature elite female sailors competing on the Severn River in J/22s. The event, running from June 4–7, includes a double round-robin format followed by knockout stages. This historic regatta celebrates women in sailing and continues its legacy after a successful 2023 revival. Competitors from around the world will participate.
June 5th, 6 p.m.; Fluegel Alumni Center, Annapolis
Whether you're a fashion enthusiast, fashionista, or foodie, catch the must-attend event of the season! Watch as models from our community strut the runway in chic daywear, black-tie elegance, and resort-ready looks from beloved local clothiers on Main Street and Town Center. Sample delicious fare from top restaurants and food trucks. Sip exquisite cocktails and mocktails. You’ll mix and mingle the night away!
June 5th through June 15th; Annapolis Mall
Get ready for thrills, treats, and tons of fun — the Carnival is rolling into the Annapolis Mall for nearly two full weeks of excitement! Heart-racing Carnival Rides for all ages, Classic Midway Games with great prizes, Delicious Food Wagons serving funnel cakes, cotton candy, corn dogs & more! Fun for the Whole Family!
June 5th; Annapolis Maritime Museum
The Annapolis Rotaract Foundation, Inc is excited to announce the 14th annual ROCK THE DOCK! The event will be held at the Annapolis Maritime Museum on Thursday, June 5th, 2025, from 6:00-10:00 PM. In 2024, we raised over 20,000 to benefit the Pretty Girl academy. This year’s Rock the Dock will benefit, the Anne Arundel County Literacy Council, a nonprofit organization dedicated to helping adults and out-of-school youth achieve functional levels of reading, writing, math and speaking English. They provide convenient, individualized tutoring at no cost to the residents of Anne Arundel County so they can improve their quality of life and become an integral part of their communities.
June 6th; Downtown Easton
On the first Friday of every month between April-December, the galleries of Easton extend their hours and invite you on a tour of artistic adventure. New exhibits tend to open during the First Friday Gallery Walk, meet & greets with artists or guest speakers are scheduled, and gallery owners will serve lite bites and spirits.
June 6th and 7th; Anne Arundel County Fairgrounds, Crownsville
This years festival has a lineup you can't miss! Young the Giant, Milky Chance, The Maine, Third Eye Blind, Hot Mulligan, The Starting Line and so many more all over two days in Crownsville.
Chesapeake Bay Motoring Festival
June 7th and 8th; Kent Island Yacht Club, Chester
Building on the success of last June’s glorious Two-Day Event please join us for the Annual Chesapeake Bay Motoring Festival, a celebration of Motoring Excellence on Maryland’s Eastern Shore. Our volunteers are diligently working to provide you another 2 days of an exciting and eclectic grouping of Muscle Cars, Hot Rods, and Classic Motorcars of all kinds enhanced by Classic Yachts and Antique Speed Boats to set a mood of going back in time. Kent Island Yacht Club, is the perfect setting to host a weekend of Camaraderie and Motoring Excellence. We invite you to enjoy antique – classic – cars – boats, along the Yacht Club’s picturesque waterfront lawn on the first Saturday and Sunday, in June. Leading up to and as a preview to Sunday’s Award Ceremony, our celebration begins on Saturday Morning with Cars and Coffee at 8:30 am for registered entrants and ticket holders, with gates opening for attendees at 10:00am. Kent Island Yacht Club will feature Antique Yachts and Classic Boats, many notable and prestigious automobile clubs from the Chesapeake Region and beyond will exhibit member’s American Classic, Corvettes and Special Interest Cars along-side a unique gathering of previous Award-Winning Motorcars to include Grand Classic, Pre-War, Post-War, Touring, and European Sports Cars, concluding with an Award Ceremony on Sunday afternoon.
June 7th, 11 a.m. to 2 p.m.; The Hotel at Arundel Preserve, Hanover
An Afternoon of Connection, Conversation, and Celebration. You're invited to join a community of women in business and leadership for our annual High Tea & High Heels event on Saturday, June 7, 2025, from 11 AM – 2 PM at the beautiful Arundel Preserve in Arundel Mills, MD. This is more than just a brunch, it’s a chance to connect with like-minded women, hear from an accomplished leader, and celebrate the contributions of women making a difference.
June 7th, 12 to 5 p.m.; Downtown Centreville
The Town of Centreville and the Maryland Wineries Association host the eighth Maryland Makers event with more ways to explore Maryland’s rich craft culture. Formerly known as DrinkMaryland, Maryland Crafted: Centreville features over 40 juried artisans and craft alcohol producers [wine, craft beer & spirits with a tasting pass ($)] plus live music and delicious food ($). Newly added: An exclusive pre-event VIP Experience ($) at Centreville's Bull & Goat Brewery with a behind-the-scenes tour, and four guided tastings with food pairings, led by event emcee and leading wine expert Laurie Forster. For tasting passes & info: MarylandCrafted.com
Naptown Philharmonic Orchestra Season Finale: Let's Play Ball!
June 7th; Maryland Hall, Annapolis
Naptown Philharmonic Orchestra’s season finale brings an orchestral experience like no other – a family-friendly sports themed concert, “Let’s Play Ball!” featuring WBJC’s Jonathan Palevsky as narrator. This program is inspired by the great all-American game of baseball, featuring timeless favorites such as Take Me Out to the Ball Game, Field of Dreams and Home Stretch familiar to audience members of all ages, from seniors to kids. And speaking of our youth, this concert also will highlight the winners of our annual, state-wide Young Artist Concerto Competition (open to all high-school students throughout the state of Maryland). It will be a heart-warming, entertaining evening for all! What a great way to bring the 2024-2025 season to a close.
Annapolis Opera Presents: Stories through Music
June 8th, 2 p.m.; Discoveries: The Library at the Mall
Every song tells a story. Learn the meanings behind classical and popular music favorites through a fun and interactive concert for all ages!
June 8th, 8 a.m. to Noon; Quiet Waters Park, Annapolis
Come to the Walk for the Animals and support the SPCA of Anne Arundel County. This family and pet friendly event has so much to offer; vendors, adoptable animals and more! Together, we can make a pawsitive difference! Register for the walk, create your fundraising page, and join us for a day of fun, furry friendship and lifesaving support.
Summer Concert Series:
Music on the Lawn - June 6th, Captain Avery Museum, Shady Side: The Freebyrds
Allen Pond Summer Concert Series - June 8th, Allen Pond Park, Bowie: Purple Flo (Hendrix Cover)
Bayside Summer Concert Series - June 8th, Downs Park, Pasadena: Dean Crawford and the Dunn River Band
17th Annual Paca Girlfriends Party
June 11th; William Paca Garden, Annapolis
Join Historic Annapolis for the social event of the season! Wander the picturesque William Paca Garden as you enjoy a glass of bubbly and indulge in culinary creations prepared by the area's premier chefs. Shop in our festive marketplace, meet and greet with local designers, and connect with a wide network of influential women.
12th Annual Chip in for the Arts Golf Tournament
June 11th; Compass Pointe Golf Course, Pasadena
Save the date for a day of fun and fundraising! Join us in supporting CAC’s arts and education programs as a sponsor, player, foursome, donor, or volunteer for our 12th Annual Chip in for the Arts Golf Tournament. Sponsorships open on February 1, so we invite businesses, organizations, and individuals to join us, play a round, and help bring the arts to everyone in our community.
June 12th; Fluegel Alumni Center, Annapolis
Each Summer, the food bank celebrates its volunteers and supporters at Feeding Hope, the organization’s signature fundraising event. In 2024, Feeding Hope raised more than $110,000 to help meet the unprecedented increase in requests for food assistance throughout the county. This year’s event will be the biggest ever, held June 12, 6-9pm, at the US Naval Academy’s new Fluegel Alumni Center. Featuring food and drinks from local restaurants, live music from Red Betty & the Ruckus, emcee Aaron Henkin (creator and host of WYPR’s The Signal and Out of the Blocks) a special can-struction project, and more!
June 14th; Philip Merrill Environmental Center, Annapolis
Bands in the Sand is the party of the year, and you won’t want to miss it! Each summer 1,600 guests gather on the beach, dance the night away to live music, and raise a drink to a saved Bay.
June 14th; Easton Firehouse, Easton
Ride the scenic roads of Talbot County Maryland! You’ll have a choice of three distances, 31.5, 40 or 61.5 miles which wind through the flat farmland and take you to water views, wooden bridges and friendly faces throughout the Eastern Shore. Day-of registration is available if space allows.
June 14th, 11 a.m. to 3 p.m.; Downtown Annapolis
Porchfest Annapolis will debut on June 14, 2025, from 11 am to 3 pm in the Germantown-Homewood neighborhood. Neighbors will volunteer their porches, stoops, or driveways, and local musicians will play for 45-minute sets. Annapolitans will be encouraged to walk from porch to porch throughout the fest to listen to the musical variety and connect with neighbors, friends, and fellow community members.
Annapolis Blues Men's Soccer Home Game - June 15th, 5 p.m.; Navy Marine Corps Memorial Stadium, Annapolis vs Northern Virginia FC
Annapolis Blues Women's Soccer Home Game - June 15th, 7:30 p.m.; Navy Marine Corps Memorial Stadium, Annapolis vs Virginia Beach United
Scenic Rivers' 36th Anniversary Hike
June 17th, 6 p.m.; Bacon Ridge Natural Area, Crownsville
Join us as we celebrate the anniversary of our very first conservation easement and the start of summer by hosting a guided hike at Bacon Ridge Natural Area. We’ll spend a beautiful evening exploring our local, protected woods and celebrating 36 years of conserving the natural, open places we all love.
Bello Machre 34th Annual Every Step Counts Walk and Bike Ride
June 14th, 8:30 a.m.; Anne Arundel Community College, Arnold
Bello Machre's annual Every Step Counts Walk & Bike Ride is a community fundraising event benefitting our mission of providing a lifetime of loving care, guidance, and opportunities for individuals with intellectual and developmental disabilities. Every dollar raised helps empower people with intellectual and developmental disabilities—and brings us one step closer to a more inclusive, connected community for all.
Antique & Classic Boat Festival & Coastal Arts Fair
June 13th through 15th; Chesapeake Bay Maritime Museum, St Michaels
The 37th Antique & Classic Boat Festival and Coastal Arts Fair is coming to the Chesapeake Bay Maritime Museum on June 13-15, inviting guests to take a step back in time in celebration of the history and artistry of these venerable vessels. Hosted by the Chesapeake Bay Chapter of the Antique & Classic Boat Society, the festival brings a sense of nostalgia to CBMM’s waterfront campus along the Miles River with one of the largest classic boat shows in the Mid-Atlantic region and more fun for the whole family. This year, the theme is “Boats in Movies and Television."
Summer Concerts:
Tides & Tunes - June 12th, 7 p.m.; Annapolis Maritime Museum, Annapolis: Dublin 5 - Irish Rock
Music on the Lawn - June 13th, 6 p.m.; Captain Avery Museum, Shady Side: Solid Sender
Avalon Outdoor Concert Series - June 14th, 7 p.m.; Avalon Theatre, Easton: US Navy Band Country Current
Bayside Summer Concert Series - June 15th, 5 p.m.; Downs Park, Pasadena: Roadducks
Allen Pond Summer Concert Series - June 15th, 6 p.m.; Allen Pond, Bowie: Clones of Funk
