Eastport a Rockin' 2025
Summer is in full swing, and there’s no better time to get out and explore all the fun happening across our region—from creative experiences and community celebrations to live music, great food, and good company. Set sail on the Wilma Lee to watch the Wednesday Night Races or sip and savor your way through a five-course wine pairing at Brampton Inn’s Grape Expectations. This week's lineup is bursting with energy, flavor, and unforgettable moments. Let’s make the most of these long, sunny days — adventure is calling!
Wilma Lee Wednesday Night Races Watch Party
June 25th, 28th ; Annapolis Maritime Museum, Annapolis
Join the Annapolis Maritime Museum crew for a two-hour extraordinary cruise enjoying the Wednesday Night Races on the Chesapeake Bay. Includes complimentary beverages (wine, beer, canned cocktails and soda).
Multi-Chamber Networking Event at the Baysox
June 26th; Chesapeake Baysox Baseball, Bowie 5:00pm – 6:30pm
"Play Ball" at Greater Severna Park and Arnold Chamber of Commerce's Multi-Chamber networking event hosted by the Chesapeake Baysox at Bowie Stadium on Thursday, June 26 at 5:00pm.
Join the Greater Severna Park and Arnold Chamber, along with the Greater Bowie Chamber, Southern AA Chamber, Northern AA Chamber, Greater Crofton Chamber, Central Maryland Chamber and the Pasadena Business Association for cocktails and baseball.
Annapolis Opera Presents: Stories Through Music
June 26th, 28th; Broadneck Community Library, Annapolis 6:00pm-7:00pm
Every song tells a story — come discover them with Annapolis Opera House!
Join the Annapolis Opera House for Stories Through Music, a lively and interactive concert experience designed especially for kids and families. This engaging program introduces young audiences to the magic of storytelling through classical and popular music favorites. Through fun narration, live performance, and audience participation, children will learn how melodies, lyrics, and rhythms come together to tell powerful stories. It’s a perfect way to spark imagination, curiosity, and a love for music — all in an entertaining and educational setting!
Grape Expectations: A Playful Plates Party at Brampton 1860
June 26th; Brampton Inn, Chestertown 6:00pm – 8:00pm
Indulge in an evening of delightful discovery at our 19th-century manor, where expertly selected fine wine and exquisite chef-crafted bites come together in perfect harmony. Savor expertly curated pairings and uncover unexpected flavors, all while immersed in the rich ambiance of history and hospitality.
Our theme for the evening is "Taste of Summer in Maryland". This 5-course small-plate menu is a celebration of the region’s finest ingredients, from its seafood to the vibrant produce that flourishes in Brampton's summer gardens. Each course is expertly paired with wine complementing and enhancing the fresh flavors. Monica Connors, WSET ® Level 3 and Regional Sales Director at DMV Distributing, LLC. will be guiding us through the pairing
2nd Star Productions Presents: Into the Woods
June 27th; Bowie Playhouse, Bowie 7:00pm – 11:00pm
James Lapine and Stephen Sondheim take everyone's favorite storybook characters and bring them together for a timeless, yet relevant, piece... and a rare modern classic. The Tony Award-winning book and score are both enchanting and touching.
The story follows a Baker and his wife, who wish to have a child; Cinderella, who wishes to attend the King's Festival; and Jack, who wishes his cow would give milk. When the Baker and his wife learn that they cannot have a child because of a Witch's curse, the two set off on a journey to break the curse. Everyone's wish is granted, but the consequences of their actions return to haunt them later with disastrous results.
Eastport a Rockin' 2025
June 28th; 2nd Street Eastport, Annapolis 11:00am – 8:00pm
Annapolis’ favorite homegrown music festival returns with 40 bands on 4 stages, showcasing a mix of beloved local acts and fresh new talent. Set along the waterfront in Eastport’s historic maritime district, the festival features a full day of live music, great food, cold drinks, and good vibes. Come celebrate the sounds of summer with the local music community!
Annapolis Blues Men's Soccer Home Game
June 28th, 7:30 p.m; Navy Marine Corps Memorial Stadium, Annapolis
The Annapolis Blues Men take on Patuxent FC in what promises to be a thrilling game full of energy and team spirit!
Annapolis Blues Women's Soccer Home Games
June 28th, 5:00 p.m.; Navy Marine Corps Memorial Stadium, Annapolis
The Annapolis Blues Women face off against Richmond Ivy in an exciting matchup you won’t want to miss!
Solstice Celebration
June 28th; Wilmer Park, Chestertown 6:00pm
Save the date for ShoreRivers' signature summer event! For more than a decade, ShoreRivers has hosted the Summer Solstice Celebration on the banks of the Chester River. Enjoy live music and dancing, refreshing cocktails, delicious food, good company, and an exceptional live auction to benefit healthier local waterways.
Brampton's Elegant Afternoon Tea
June 29th; Brampton Inn, Chester 2:00pm – 3:30pm
Our pastry chef’s creations of decadent sweet and mouth-watering savory bites are paired with a hand-picked selection of fine Harney & Sons Teas including iced tea in the warmer months. Enjoy as you and your companions spend a lovely afternoon in the peaceful elegance of the Brampton.
Summer Concert series:
Waugh Wednesdays: Summer Concert Series – June 25th; Waugh Chapel Towne Centre: Technicolor Motor Home: Enjoy all the sounds of Steely Dan.
Tides & Tunes – June 26th; Annapolis Maritime Museum: Michael Mchenry- Funk Rock
ATC Summer Concert Series – June 27th; Annapolis Town Center: Groove Spot Band
Music on the Lawn – June 27th; Captain Avery Museum: Roots &Tides
Free Avalon Outdoor Concert Series – June 28th; Avalon Theatre: Mid-shore Voices United
Bayside Summer Concert Series – June 29th; Downs Park
Allen Pond Summer Concert Series – June 29th; Allen Pond Park: David Bach – Jazz
Tunesday: Summer Concert Series – July 1st, Back Creek Annapolis: Nate Finn
