Photo by Taylor Lewis, Courtesy of Annapolis Baygrass Music Festival
Enjoy two days of live music and waterfront views at the Annapolis Baygrass Music Festival, a conservation-focused event where every ticket helps protect the Chesapeake Bay.
This week isn’t just packed — it’s overflowing. We’re talking wine-paired feasts, donkey cuddles (yes, really), the world’s largest and most celebrated pickle-themed festival, and live music that’ll keep you out past your bedtime. Whether you want to stretch it out with yoga, sip something fancy, or hit the dance floor, there’s something to match your vibe. Keep scrolling — your plans just found you.
Yin and Peaceful Yoga in Downtown Annapolis
September 18th; 17 Francis St, Annapolis 12:00pm - 1:00pm
Take a break in the middle of your week with Mid-Day Yoga, held every Thursday at 12:00 PM. This all-levels guided yoga session offers a calm and welcoming space to stretch, move, and reset. Participants can extend their wellness time for up to an hour with optional self-guided practices such as breathwork, journaling, and quiet stretching, included with registration. Perfect for beginners and experienced yogis alike, this class is a simple way to relax, recharge, and return to your day feeling balanced and energized.
Grape Expectations: A Playful Plates Party” at Brampton 1860
September 18th; 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 "Autumn Harvest". Our 5-course small-plate menu is a fun and delicious take on fall favorites. Each course is expertly paired with wine, complementing and enhancing the delicious flavors, delivering an experience as fun and memorable as your best fall gathering. Nikki Sands from Breakthru Beverage Group will be guiding us through the pairing.
Paint & Pet Nite
September 18th; Campbells Lane Farm, Easton 6:00pm – 8:00pm
Join us for a fun evening painting and cuddling with donkeys. By the time you leave you will have painted an 8 x 10 painting of “Boo”, one of the sweetest donkeys you will ever meet, and gotten a few good cuddles from the donkey herd. Your creativity will flow under the gentle guidance of Nichole, she will have you feeling relaxed and confident so your inner artist can come alive. No prior painting experience needed! Bring a drink, bug spray, wear closed toed shoes, no sandals, flip flops, or crocs please. Leave feeling lighter and refreshed.This event is designed for ages 12 and up.
Colonial Cocktails: Medicinal Mixers
September 18th; Historic London Town and Gardens, Edgewater 6:30pm – 7:30pm
Step back in time and explore the spirited side of history at this 21+ event featuring Dr. Salmon’s Punch and classic mint juleps. Guests will learn about alcohol’s fascinating role in history while sampling these historic cocktails in a lively, social setting. Tickets are $26 for members and $34 for non-members.
Music Bingo FUNdraiser
September 19th; Homestead Gardens, Davidsonville 5:30pm – 8:00pm
Music Bingo FUNdraiser at Homestead Gardens! Get your listening ears ready for a fun night of Music Bingo at Homestead Gardens on Friday, September 19th. 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!
Calm for a Cure - Party for a Purpose
September 19th; Pherm Brewing, Crofton 6:00pm – 10:00pm
We invite you to join us for Calm for a Cure, a special fundraising event benefiting the Harmony Foundation’s charitable initiative dedicated to providing complimentary wellness services for individuals navigating cancer and the caregivers who support them. Our mission is to ensure year-round access to massage, skincare, and restorative care, offering comfort and healing during some of life’s most difficult challenges. This unforgettable evening will bring together community, compassion, and celebration—all in the spirit of giving back.
Donkeys and Dahlias
Septemeber 19th; Campbells Lane Farm, Easton 6:00pm – 8:00pm
Enjoy all the delight that comes with combining dahlias and donkey cuddles. Transform a pumpkin into a stunning dahlia centerpiece using local Vintage Family Farms’ blooms. Finish the evening with donkey cuddles to give you the best feelings at this fall-tastic event. If you plan to spend time with the donkeys, please have closed toed shoes, no sandals or crocs. Bring all your friends and family for this unique experience!
Designer Purse Bingo to Benefit CAC
September 19th; Elks Lodge #2482, Annapolis 7:00pm – 10:00pm
Join the fun at Severna Park Elks Lodge for Designer Purse Bingo to benefit the Chesapeake Arts Center. Play 16+ games for the chance to win designer purses and accessories from Coach and Michael Kors, plus enjoy door prizes, basket raffles, and cash raffles throughout the night. Food and drinks will be available for purchase. Doors open at 6:00 PM, with tickets $35 in advance or $40 at the door. Reserved tables for groups of 8–10 are available. Ages 18+.
Annie
September 19th; Compass Rose Theater, Annapolis 8:00pm – 10:15pm
The beloved family musical Annie takes the stage this fall, telling the heartwarming story of a spirited orphan, her loyal dog Sandy, and her journey to find her parents—along the way visiting the grand mansion of billionaire “Daddy” Warbucks. Performances run Fridays, Saturdays, and Sundays, with evening and matinee shows through mid-October, making it the perfect outing for theater lovers of all ages.
For the Love of the Library
September 19th; Michael E. Busch Annapolis Library, Annapolis 8:00pm – 10:30pm
Celebrate the power of stories, community, and lifelong learning at Anne Arundel County Public Library’s largest fundraising event of the year. For the Love of the Library takes place on Friday, September 19, and features an evening of inspiration and celebration to support the library’s programs and services. This signature event brings together library lovers, community leaders, and supporters for a memorable night dedicated to advancing access to knowledge for all.
Annapolis Baygrass Festival
September 20th-21st; Sandy Point State Park, Annapolis
Enjoy two days of live music and waterfront views at the Annapolis Baygrass Music Festival, a conservation-focused event where every ticket helps protect the Chesapeake Bay. This unique festival blends progressive bluegrass, jamgrass, and Americana performances with a beautiful beachfront setting. Along with outstanding music, Baygrass raises awareness for mental health initiatives and celebrates the Chesapeake Bay community, making it a weekend of fun with a meaningful purpose.
The Big Dill World's Largest Pickle Party
September 20th; Power Plant Live, Baltimore
The Big Dill, the world’s largest and most celebrated pickle-themed festival, returns to Power Plant Live! on Saturday, September 20 and Sunday, September 21, bringing Baltimore its sixth annual brine-soaked bash as part of the national “In My Pickle Era” Tour. Timed perfectly with the Baltimore Ravens’ Monday Night Football appearance, this year’s festival gives fans an entire weekend to dive into the most, flavorful, fun and wildly entertaining celebration of pickles on the planet. Guests can expect unlimited pickle sampling from top national and regional brands inside Pickle Row, along with Baltimore’s most outrageous pickle-infused foods.
Boatyard Beach Bash
September 20th; Annapolis Maritime Museum, Annapolis 4:00pm – 10:00pm
Experience a night of island vibes with music by Jimmy Buffett’s Coral Reefer Band and other world-class musicians. Guests will enjoy an open bar and a delicious meal as part of this special waterfront event. Proceeds benefit the Annapolis Maritime Museum’s educational programs, supporting efforts to connect the community with the rich maritime heritage of the Chesapeake Bay.
Baltimore Symphony Orchestra's Season Opening Gala
September 20th; Joseph Meyerhoff Symphony Hall, Baltimore 8:00pm – 10:00pm
The two-night Season Opening Gala will feature acclaimed violinist Joshua Bell. The concerts, held on September 19 at The Music Center at Strathmore and September 20 at the Joseph Meyerhoff Symphony Hall, will showcase a colorful and alluring bouquet of French masterpieces, including Saint-Saëns’s Violin Concerto No. 3, Massenet’s Méditation from Thaïs, and orchestral selections from Bizet’s Carmen. These evenings promise unforgettable performances, including collaborations with the Baltimore Symphony Youth Orchestras and BSO OrchKids, setting a celebratory tone for the season.
Naptown Philharmonic; Music of the Americas: A Celebration of Life & Culture
September 21st; Maryland Hall for the Creative Arts, Annapolis
The season opens on Sunday, September 21, with Music of the Americas: A Celebration of Life & Culture at Maryland Hall. Led by Music Director and Conductor Anna Binneweg, this festive concert honors Hispanic Heritage Month with a program featuring the vibrant and diverse musical traditions of Latin America. Designed to be familiar, fun, and family-friendly, the performance invites the community to experience the joy and energy of live orchestral music in an inspiring setting.
Ride for Clean Rivers
September 21st; Chesapeake College, Talbot County 8:00am
Save the date for our 21st Ride for Clean Rivers and your chance to ride the beautiful back roads of Talbot and Queen Anne’s counties in support of ShoreRivers’ work for clean waterways. This is a great way to bring summer to a close while also supporting a great cause.
Ballet in the Garden
September 21st; Hammond Harwood House, Annapolis 5:00pm – 6:00pm
Before Ballet Theatre of Maryland kicks off its performances in residence at Maryland Hall, the company will open its season with Ballet in the Garden at the historic Hammond-Harwood House on September 21st. Guests can enjoy complimentary wine, mingle in a welcoming setting, and experience a mix of beloved and rare dance works in an intimate atmosphere.
An Evening with Elin Hilderbrand
September 22nd; Talbot County Free Library, Easton
Spend an elegant evening with international bestselling author Elin Hilderbrand at the Oaks Waterfront Hotel in Royal Oak, Maryland. Guests will receive a copy of Hilderbrand’s newest release, The Academy—a colorful tale of New England boarding school life co-written with her daughter, Shelby Cunningham. Enjoy complimentary wine, upscale hors d’oeuvres, and a lively author talk, followed by a book signing and photo opportunity. The evening also includes a cash bar and local vendor booths from Smokey Cat Lavender Farm, Wrabyn Boutique, and Browse about Books.
