Photograph courtesy Annapolis Baygrass Music Festival
The Annapolis Baygrass Music Festival is a conservation-focused musical event where just by having fun you're helping to Save the Chesapeake Bay.
September 18th, 5:30 p.m.; Pusser's Caribbean Grille, Annapolis
Green Drinks is a get-together for people who care about the Environment. Meeting casually is the best way to get to know one another and pull together locally for our planet.
Raising the Curtain: Season Opening Celebration
September 19th, 6:30 p.m.; Byzantium Banquet Center, Annapolis
Sip crafted cocktails, feast on tropical cuisine, enjoy performances, and experience Annapolis Opera’s season-opening like never before! Explore the opera world through wonderful music, dine on tropical cuisine, and celebrate opera as we raise the curtain on the season in a night you won’t forget!
September 19th; Annapolis Maritime Museum
The Taste is a celebration of our Chesapeake Bay watershed, offering live music, locally-inspired eats, awards, silent auctions, and camaraderie. As Alliance for the Bay's largest annual fundraiser, the Taste aims to bring together like-minded corporations and conservationists within three distinct Chesapeake Bay watershed communities.
USNA Blues & Gold at Radford Terrace
September 19th, 7 p.m.; Radford Terrace on USNA Campus, Annapolis
Under the direction of Senior Chief Musician Rory Cherry, Blues & Gold will perform classic blues and blues-infused music by artists such as Freddie King, Little Milton, and Otis Redding, and more recent hits by Chris Stapleton and Joe Bonamassa.
Haven Ministries Annual Golf Tournament
September 20th, 7:30 a.m.; Prospect Bay Country Club, Grasonville
Registration and Sponsorships open! Our annual golf tournament is presented by Construction Services & Supply to benefit Haven Ministries. Enjoy a great day of golf while supporting Haven Ministries to provide HOPE through Shelter, Clothing, Food and Support to those in need in Queen Anne's County.
September 20th; Homestead Gardens, Davidsonville
Get your listening ears ready for a fun night of Music Bingo at Homestead Gardens on Friday, September 20th. The music bingo FUNdraiser benefits Girls on the Run of the Greater Chesapeake's scholarship fund by increasing program access and bringing confidence to more girls! Bring your family and friends to test your knowledge of song titles from various music genres and the chance to win fun prizes! Plus, you can check out Homestead Garden's new Beer Garden and grab pizza from a family-run pizza truck.
FINAL Annapolis Town Center Summer Concert
September 20th, 6 p.m.; Annapolis Town Center
Join for the last concert of the summer, from 6pm-8pm for family friendly live music at the Boathouse Pavilion in the East Village (located next to P.F. Chang’s). A performance line up you don’t want to miss: Lower Case Blues
Chesapeake Cycling Club's Rolling Donuts
September 21st; Tuckahoe State Park, Queen Anne
A sweet late-season cycling event through the bucolic farmland and pastural countryside of Maryland's Eastern Shore. Flat, fast, and fun!
September 21st; Kent Island Fire Department, Chester
Come together for the 45th Annual Chesterwye Gala - Featuring a surf & turf plated dinner, dancing, and auction! Hosted on Saturday, September 21st at the Kent Island Fire Department, Chester, MD. Festivities kick off at 5pm
September 21st and 22nd; Sandy Point State Park
The Annapolis Baygrass Music Festival is a conservation-focused musical event where just by having fun you're helping to Save the Chesapeake Bay. Baygrass blends the finest progressive bluegrass music with a gorgeous beachfront venue and a core mission to protect and restore the Bay. You'll enjoy 14 top touring bands on 2 stages over 2 days, delicious local food, microbrews, wines, craft cocktails/mocktails, workshops, craft vendors, and fun activities for all ages
September 21st; Boatyard Bar and Grill, Annapolis
Boatyard owner, Dick Franyo is on the Board of the Annapolis Maritime Museum and had a vision for a fund/fun raiser with a Jimmy Buffett/Parrot Head theme. Dick is a Parrot Head and looked hard at the Jimmy Buffett's model of selling a lifestyle/entertainment/escapism venue when he started the Boatyard. He felt that this event could be different than other local musical fundraisers and that Parrot Heads would be enthusiastic supporters.This event raises over $100,000 net of expenses for the Annapolis Maritime Museum
September 21st; Crofton Country Club
Greater Crofton Chamber of Commerce is hosting their Festival on the Green again this fall! Get ready for a day for the whole family to enjoy.
September 21st; Virtual Event
GiGi’s Playhouse is the ONLY international network of Down Syndrome Achievement Centers created to provide FREE, life-changing therapeutic and educational programs for all ages of development and for the unique needs of individuals with Down syndrome. Join a team of experienced educators and therapists from across the GiGi’s Playhouse Network to learn how to teach individuals with Down syndrome the way they learn best. Since 2003, we have been working nonstop to empower individuals with Down syndrome to reach their full potential and move toward independence.
Navy Football Home Game vs Memphis
September 21st, 3:30 p.m.; Navy-Marine Corps Memorial Stadium, Annapolis
Saturday is the third of three-consecutive home games for the Mids. It's the first time Navy has opened the season playing three-straight home games since 1988 when the Mids opened up against James Madison, Delaware and Temple.
Naptown Philharmonic Concert - A New Chapter Begins
September 21st; Maryland Hall, Annapolis
A New Chapter Begins for the Naptown Philharmonic Orchestra on September 21 as Music Director/Conductor Anna Binneweg picks up the baton to kick off the 2024-2025 season with a concert to honor Hispanic Heritage Month, Unity and Resilience. The concert will showcase the rich musical repertoire of Latin America along with other, well-known compositions.
September 21st through 22nd, 28th through 29th, October 5th through 6th, 12th through 13th, 19th through 20th; Maryland Renaissance Festival Fairgrounds, Annapolis
Unique among most festivals, including renaissance festivals, the Maryland Renaissance Festival utilizes a storyline and progresses each year forward in the timeline of Henry VIII, through all his reign and all six of his wives. This season the year is 1536, and as ever, the King’s love life is the source of gossip. The royal story is played out in stage shows and in improvisations throughout the festival grounds.
September 22nd, 11 a.m. to 4 p.m.; West Street, Annapolis
Get ready for this year’s Oktoberfest, where we welcome RAR Brewing and Chessie's Wharf as our beer garden sponsor! Enjoy a cold beer, great food from a variety local restaurants and food trucks, PLUS get a head start on holiday shopping! Family friendly, there's something for everyone.
GiGi's Playhouse Golf Tournament
September 23rd, 8 a.m.; Queenstown Harbor Golf Course
GiGi’s Playhouse is a 501(c)(3) nonprofit organization with a mission to change the way the world views Down syndrome. We provide educational, therapeutic-based and career development programs for individuals with Down syndrome, their families and the community, always free of charge.
September 26th; William Paca House and Garden, Annapolis
Connect with a wide network of influential men - the region's top business leaders, entrepreneurs, professionals, and visionaries representing our diverse community - in the picturesque William Paca Garden. While you network, enjoy bourbon, whiskey, and other fine liquor tastings, premium cigars, and delightful food from the area’s top chefs.
Hospice of the Chesapeake Annual Golf Tournament
September 26th; Queenstown Harbor
The golf tournament is held annually in the Fall at Queenstown Harbor Golf Course. This event typically draws more than 200 area golfers and raises $100,000 to support the mission of Hospice of the Chesapeake.
Mid-Atlantic Symphony Orchestra's Violin Virtuoso
September 26th, 7:30 p.m.; Easton Church of God
The Mid-Atlantic Symphony Orchestra kicks off its 27th season as the Eastern Shore’s only professional symphony orchestra with its season opening concert, “Violin Virtuoso,” on Thursday, September 26, at 7:30 p.m. at the Church of God in Easton. This concert is one of 25 Masterworks full orchestra concerts and eight Ensemble concerts being offered between September and May.
Dorchester Chamber Challenge Golf Tournament
September 27th; River Marsh Golf Club, Cambridge
The Dorchester Chamber of Commerce will host its 34th annual Chamber Challenge Golf Tournament on Friday afternoon September 27, 2024. The golf tournament offers a superb opportunity to network with business owners and leaders from across the region, while enjoying 18 holes of golf at the Hyatt Regency Chesapeake Bay Resort and Spa.
September 27th, 28th, 29th; Anne Arundel Community College, Arnold
Come see AACC Theatre from a different perspective! Join AACC Theatre for their staged reading of the award-winning play "Proof".
St. Michales Concours d'Elegance
September 27th through 29th; Kent Island Yacht Club, Chester
The picturesque waterfront lawn of the Kent Island Yacht Club will be the backdrop for the 17th annual St. Michaels Concours d’Elegance on Chesapeake Bay on Sunday, September 29. The event is presented by Bentley Motors and sponsored by Porsche Annapolis, with Porsche Annapolis also serving as the exclusive sponsor of this year’s motoring tour and welcome reception.
Friends of Blackwater Wild Goose Chase Women's Bicycle Ride
September 28th through 29th; Blackwater National Wildlife Refuge, Cambridge
Women bicyclists from all over the Mid-Atlantic and beyond converge on Dorchester County to ride in the Wild Goose Chase Women's Bicycle Ride. Cyclists can ride along low-traffic scenic county roads in and around Blackwater National Wildlife Refuge (NWR). Since women's bicycling pioneer Georgena Terry created the event in 2008, the Wild Goose Chase has raised over $190,000 for the Friends of Blackwater, which has used the funds to support numerous Refuge projects. The contact people are Sue Fischer and Sherry Murray at BlackwaterWGC@gmail.com.
Pumpkin Patch for the Light House
September 28th through October 27th; St. Martin's Lutheran Church, Annapolis
An Annapolis tradition of community coming together! Each October, the Friends of the Light House teams up with volunteers from different local groups and churches to host a Pumpkin Patch at St. Martin’s on Spa Road. Find your fresh Eastern Shore pumpkin through October 27th from 10 a.m. to 6 p.m. on weekends and from 2 p.m. to 6 p.m. on weekdays, all to benefit the Annapolis Light House, a homeless prevention and support center. Find more information at friendslhs.org
September 28th through 29th; Byzantium Banquet Center, Annapolis
Your local home festival is at the Byzantium Event Center in Annapolis on February 24th and 25th. Find contractors and service companies in your area to create your dream home, find inspiration and participate in educational seminars with local and national home experts.
Anne Arundel County Literacy Council Annual Book Fair
September 28th, 10 a.m.; Westfield Annapolis Mall
The Anne Arundel County Literacy Council (AACLC) will host its 4th-annual fundraiser book fair outside Discoveries: The Library at the Mall at the Crate & Barrel Court in Annapolis Mall. The fair will feature 100s of gently used books, including children’s books, cookbooks, bestsellers, romance novels, memoirs, mysteries, thrillers, historical fiction, and much more. Books will be priced at $2 for hardbacks and $1 for paperbacks. Shoppers can fill a special edition Literacy Council tote bag with books for $20. PayPal, Venmo, credit cards, checks, and cash will be accepted. Also at the book fair — gift basket raffles and more. Proceeds from the book fair will support the Council’s free adult tutoring programs in Anne Arundel County.
September 28th, 5:30 p.m.; Chesapeake Bay Environmental Center, Grasonville
Ticket purchases and sponsorships benefit CBEC’s Reef Restoration and Education Initiatives, including: Creating new habitats for wildlife, Providing paid summer internships for college students, Transforming disadvantaged youth into future stewards of the Bay through summer camp scholarships, Upgrading onsite interpretive experiences for general visitors
31st Annual BGCAA Bob Ferry Golf Classic
September 30th; The Golf Club at South River, Edgewater
Enjoy a day on the links, including a putting contest, closest to the pin contest, food and drinks, and much more. We look forward to seeing you then!
September 30th; Talbot Country Club, Easton
For over 30 years, our annual Charity Golf Classic tournament has raised more than $1 million to provide resources for the children and adults living with developmental disabilities and autism that Benedictine supports. Please check back for registration and sponsorship opportunities. For more information, please contact Caroline Bauerle at caroline.bauerle@benschool.org or 410 634 2292.
