Photo credit: Kenneth Tom
You are invited to join Historic Annapolis for the 12th annual Blazers . Bourbon . Cigars on Thursday, September 25, 2025 from 6 pm – 9 pm in the picturesque William Paca Garden.
Your Weekend Starts Here!! Fall is calling, and this week’s lineup is serving everything from charity golf tournaments and classic car shows to bourbon-and-cigar soirées, book fairs, and festivals that’ll have you shopping, sipping, and soaking up the season. Whether you’re hitting the greens, hitting the dance floor, or just hitting “add to calendar,” there’s no excuse for staying in. Scroll on, pick your plans, and let’s make this week one for the highlight reel.
Evolve KidsCare Charity Golf Tournament
September 24th; Compass Pointe Golf Course, Pasadena 8:00am – 4:00pm
Please join us on Wednesday, September 24, 2025 at Compass Pointe Golf Course in Pasadena, MD for our Annual Charity Golf Tournament. Evolve KidsCare is a nonprofit in Anne Arundel County providing free childcare to families in recovery from substance use disorder. This is an incredible opportunity to raise needed funds that will help make a difference in the lives of many children & families in our communities.
Hospice of the Chesapeake Annual Golf Tournament
September 25th; Queenstown Harbor, Queenstown, 8:00am – 5:00pm
Tee off for a cause at the Annual Golf Tournament benefiting Hospice of the Chesapeake, held Thursday, September 25, at the scenic Queenstown Harbor Golf Course. This popular charity event includes breakfast, lunch, beverages on the course, an awards banquet, greens fees, range time, and a $50 gift to use at the mobile TaylorMade Pop-Up Shop. Registration begins at 9:00 AM, with a 10:00 AM shotgun start. Proceeds support Hospice of the Chesapeake’s programs and services across Anne Arundel, Calvert, Charles, and Prince George’s counties, bringing comfort and care to those who need it most.
Blazers. Bourbon. Cigar
September 25th; William Paca House and Garden, Annapolis 6:00pm – 9:00pm
Join Historic Annapolis at the 12th annual Blazers. Bourbon. Cigars! Connect with a wide network of influential community members – 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 and restaurants. This popular annual fundraiser supports Historic Annapolis and our mission to Preserve. Protect. Connect.
St. Michaels Concours d’ Elegance
September 26th; Kent Island Yacht Club, Kent Island 6:30am – 4:00pm
The St. Michaels Concours d’Elegance returns September 26–28 at its new location, the Kent Island Yacht Club. This elegant waterfront event showcases rare and award-winning classic cars, including a special celebration of the 100th anniversary of the Rolls-Royce Phantom, plus a class featuring past Best of Show winners. Guests can enjoy gourmet food and drinks, live music, and a stunning collection of vintage automobiles and yachts, all set against the scenic backdrop of Kent Island.
Jazz in the Garden
September 26th; Fig & Flower, Annapolis 6:00pm – 7:30pm
Enjoy a night of live music in the garden as jazz guitarist Ahmed Warshanna and his trio perform selections from his upcoming EP, Introducing… Ahmed Warshanna! This intimate outdoor concert invites guests to relax on the lawn or at bistro tables while exploring the rich textures and nuances of Warshanna’s music. Guests are welcome to bring their own food and drinks or purchase light snacks and beverages on site. During the event, Fig & Flower will offer 10% off all retail items and flowers for a perfect evening of music and browsing.
Annie
September 26th; Compass Rose Theater, Annapolis
The beloved family musical Annie takes the stage this fall, following the story of a spirited orphan, her loyal dog Sandy, and her quest to find her parents. Along the way, she meets billionaire “Daddy” Warbucks and discovers the true meaning of family and hope. Performances are held Fridays, Saturdays, and Sundays, with evening and matinee shows running through mid-October—perfect for theater lovers of all ages.
Donate Life Family Fun Run presented by Infinite Legacy
September 27th; Camden Yards Sport Comple, Baltimore 7:00am – 12:00pm
Now in its 17th year, the Donate Life Family Fun Run brings together donor families, transplant recipients, waitlist candidates, living donors, hospital partners and supporters to celebrate organ, eye and tissue donation and to benefit Infinite Legacy’s outreach, education and donor family aftercare. Participants can run or walk a timed 5K on a scenic course around Camden Yards Sports Complex and Downtown Baltimore—or walk a ~1K walk looping the stadium from Lee Street. Before and after the race, enjoy music, local food trucks with a picnic area, sponsor booths, a photo booth, kids’ games and face painting, the “Why We Walk” tribute tent, T-Shirt Row honoring donors and recipients, an official merchandise table and a Donor Family Booth offering mental health resources.
Anne Arundel County Literacy Council Annual Book Fair
September 27th; Annapolis Mall, Annapolis 10:00am – 4:00pm
The book fair offers thousands of gently used books in multiple genres — $1/paperback, $2/hardback, $25 for a special edition tote to fill — and raffle baskets ($1 to $5/ticket) to raise funds for free Literacy Council programs. It is a wonderful community gathering in a large indoor courtyard at the mall. A children's activity will be offered at the Discoveries Library during the book fair.
Fall Festival on the Green
September 27th; Crofton Country Club, Crofton 10:00am
The Festival on the Green returns this fall with one of the area’s most popular community events, drawing 2,500–3,000 attendees. This seasonal tradition features a wide variety of vendors, local businesses, and sponsors, offering a full day of shopping, food, and family fun. Held twice a year, in spring and fall, the festival is a favorite for both visitors and participants looking to enjoy the best of the season.
Music by the Marsh; Celebrating 40 years at Jug Bay Wetlands Sanctuary
September 27th; Emory Water Nature Preserve, Lothian 2:00pm – 7:00pm
Join Anne Arundel County Recreation and Parks and Jug Bay Wetlands Sanctuary in celebrating 40 years of protecting 1,700 acres of unique habitat and wildlife along the Patuxent River through education, research, stewardship, and volunteering. Enjoy a day filled with live music, art and archaeology exhibits, kids activities (Touch a Truck, Hay Stack Climb, crafts), photo booth, lawn games, pollinator garden & meadow walks, the unveiling of our 40th anniversary poster, and food trucks.
Anchors & Artisans Market
September 28th; Annapolis Town Center, Annapolis 11:00am – 4:00pm
Spend a Sunday supporting local makers at Anchors & Artisans, held the fourth Sunday of each month through October from 11:00 AM to 4:00 PM at Annapolis Town Center. This family-friendly market features 40+ local vendors offering handmade goods, artwork, pottery, jewelry, and more. Guests can enjoy live music, face painting, and food and drinks from local businesses while browsing unique products. Located near the Boathouse Pavilion and Tatte, it’s the perfect way to shop small and spend a fun afternoon outdoors with family and friends.
