Photo Courtesy of Annapolis Boat Shows
Fall fun is in full swing — and this week’s lineup proves it!
From bluegrass beats in blooming gardens to champagne toasts and sailboats on the bay, this week is bursting with everything that makes October in Maryland magic. We’re talking film festivals and art fairs, reggae and wine weekends, coastal parties that keep the harbor rocking, and elegant dinners worth every sip. Whether you’re chasing live music, local makers, or the next reason to raise a glass — this week’s events have you covered. Scroll on… adventure (and maybe a little rosé) awaits.
Garden Ramble Music Event: Featuring the Black-Eyed Suzies
October 8th; Historic London Town and Gardens, Edgewater 5:30pm – 8:00pm
Wander through Historic London Town and Gardens' 10-acre gardens, enjoy delicious drinks, and revel in live music stations scattered throughout the grounds. Take in the beautiful fall colors while sipping on tasty beverages. 5:30pm – 6:30pm, ramble through the gardens and enjoy live music as Annapolis Bluegrass members jam throughout our gardens. At 7:00pm, gather at our main stage for a showcase performance by the Black-Eyed Suzies. 21+ event, one drink ticket included.
Annapolis Sailboat Show
October 9th – 13th; Annapolis City Dock, Annapolis
Sailors from around the globe gather in downtown Annapolis every October for the Annapolis Sailboat Show, one of the premier sailing events in the world. This annual celebration features floating docks lined with sailboats of every kind—multihulls, monohulls, cruisers, racers, and dinghies—along with tents showcasing the latest nautical gear, accessories, sails, rigging, electronics, and more. Whether you’re a seasoned sailor or just beginning your journey, the Sailboat Show offers a chance to expand your horizons, discover new opportunities, and connect with fellow sailing enthusiasts in a world-class setting.
Play with a Purpose
October 9th; Woodholme Country Club, Pikesville 12:00pm – 4:00pm
Join the Erin Levitas Foundation on Thursday, October 9, 2025, at Woodholme Country Club for Play with a Purpose, a day of games and giving back. Families, friends, and community supporters will gather to raise awareness for body safety and boundaries in the fight to prevent sexual harm. Guests are encouraged to bring their favorite games—mahjong, canasta, Mexican train, or bridge—and enjoy an afternoon of connection and fun. The event also includes a catered lunch, raffles, and access to prevention resources. Hosted by Foundation co-chairs Susan Lawson and Jordan Higgins, this uplifting event combines camaraderie with an important mission: supporting sexual violence prevention and education.
Chesapeake Film Festival
October 10th – 12th; Downtown Easton, Talbot County
The Chesapeake Film Festival returns October 11–12, bringing film lovers to Easton for its 18th season. Screenings at the Ebenezer Theater, Academy Art Museum, and Talbot County Free Library will feature shorts, documentaries, student films, and international features. Special guests include Emmy Award-winner Vincent De Paul, John O’Hurley of Seinfeld, and film consultant Rebekah Louisa Smith. Highlights include filmmaker Q&As, student and environmental film blocks, a live podcast with Casting Confidential, and screenings such as Anatomy of a Fall (Palme d’Or, Cannes 2023), Strangers, and Holding Liat. With films, panels, and receptions, CFF offers a weekend of cinema, culture, and conversation on Maryland’s Eastern Shore.
Annapolis Symphony presents A New World with Pablo Sainz-Villegas, guitar
October 10th; Maryland Hall, Annapolis 7:30pm – 10:00pm
Internationally renowned Spanish guitarist Pablo Sainz-Villegas joins Maestro José-Luis Novo and the Annapolis Symphony Orchestra for a rare evening of Spanish artistry and symphonic brilliance. The program features Arturo Márquez’s new guitar concerto Mystical and Profane, written specifically for Sainz-Villegas, alongside Reinaldo Moya’s Polo Romanesco and Dvořák’s beloved New World Symphony. A pre-concert lecture by WBJC’s Jonathan Palevsky will be offered free to ticket holders. Tickets start at $25, with $10 student tickets and discounts available for military, law enforcement, and first responders.
Art @ The Park's 35th Anniversary
October 11th – 12th; Quiet Waters Park, Annapolis 10:00am – 4:00pm
Celebrate the 35th year of Art @ the Park at Quiet Waters Park in Annapolis. This beloved arts festival brings together live music, visual arts from ceramics and woodwork to photography, jewelry, and painting, plus food trucks, performances, and demonstrations. Families will enjoy kid-friendly activities, and leashed pets are welcome too. With creativity around every corner, Art @ the Park is a can’t-miss community tradition.
2025 Autumn Reggae Wine & Music Festival at Linganore
October 11th – 12th; Linganore Winery, Annapolis 8:00am
Dive into island vibes at Linganore Wine cellars’ 2025 Autumn Reggae Wine & Music Festival, the longest-running reggae festival on the East Coast. Enjoy two full days of live performances, authentic island cuisine, local artisan vendors, and unlimited wine sampling from Linganore Wine cellars. Headliners include the Kurlou Reggae All Stars, Mighty Joshua, and Nkula Band, with DJ Sprang International keeping the music flowing all weekend long. Guests can also shop from more than 40 local vendors, savor Caribbean flavors, and relax with a glass of wine while soaking in the rhythms of reggae. VIP ticket holders receive all the perks of general admission plus exclusive tastings, early entry, indoor seating, and additional amenities for a truly elevated festival experience. Discounts are available for military, designated drivers, and young adults ages 18–20.
Holistic Fall Festival
October 11th; Cambells Lane Farm, Easton 9:00am – 3:00pm
Celebrate the season with a day of fun, creativity, and connection at the Holistic Fall Festival! This community gathering offers something for everyone, blending wellness, local artistry, and family-friendly activities in a vibrant fall atmosphere. Festival highlights include free donkey cuddling, alpaca meet-and-greets from Outstanding Dreams Farm, and a community interactive mosaic art project. Kids will love the bounce house, bathtub rides, and hay rides, while adults can explore the artisan market, enjoy the flower bar from Vintage Family Farm, and connect with wellness practitioners offering unique insights and services. Delicious food vendors will be on-site to keep you fueled throughout the day, making it the perfect outing for families, friends, and neighbors.
Party in the Port
October 11th; Eastport Yacht Club, Annapolis 6:00pm – 10:00pm
Eastport Yacht Club’s signature boat show bash is back with a night of high-energy music, food, and celebration on the Annapolis waterfront. Headlining the evening is Misspent Youth, the powerhouse cover band known for delivering dance rock hits from the ’80s to today. With soaring harmonies, ripping guitar solos, and two Maryland Music Awards nominations, they’ll keep the dance floor rocking from start to finish. This year’s Party in the ‘Port also honors the Valhalla Sailing Project’s 10th Anniversary, celebrating a decade of empowering veterans through the healing power of sailing. Guests can enjoy delicious burgers, hotdogs, and EYC’s legendary libations while soaking in the lively atmosphere with friends. More than just a party, this event is a celebration of music, community, and the spirit of sailing—a night that will echo across the harbor!
2025 OBI Mardi Gras Masquerade
October 11th; Opportunity Builders Inc, Millersville 6:30pm – 11:00pm
Let the good times roll at OBI’s 26th Annual Mardi Gras Masquerade on Saturday, October 11—a night filled with music, flavor, and festive spirit, all in support of a great cause. This beloved annual event brings the vibrant energy of New Orleans to Anne Arundel County, featuring Cajun-inspired food and drinks, an expansive silent auction, and roaming entertainers that will transport you straight to Bourbon Street. Guests can enjoy lively games, exciting prizes, and a chance to dance the night away to the incredible sounds of Oracle, one of the region’s premier variety bands. All proceeds benefit Opportunities Builders, Inc. (OBI), supporting youth and adults with disabilities who depend on OBI’s programs year-round. Celebrate, give back, and experience a night of unforgettable fun—all for an extraordinary cause.
Providence of Maryland’s Annual Harvest Bash – Oktoberfest Edition!
October 11th; Providence’s Greenhouse, Arnold 7:00pm – 9:30pm
Join us for a festive evening of food, drink, music, and community at Providence’s annual Harvest Bash – Oktoberfest Edition. This lively celebration features entertainment by the Dan Haas Band, traditional Bavarian cuisine and cocktails, exciting raffles and live auctions, and seasonal shopping with Providence Pottery and fall décor. Guests can also enjoy the cozy Fireside Biergarten and more. The Harvest Bash is a vital fundraiser supporting Providence of Maryland’s mission to empower over 300 individuals with intellectual and developmental disabilities across Anne Arundel and Charles counties. Proceeds directly fund programs that help people gain meaningful employment, develop skills, and engage in their communities with dignity and purpose.
Historic Annapolis, Banneker-Douglass-Tubman, & Maryland Hall Present: Abby Phillip
October 12th; Maryland Halll for Creative Arts, Annapolis 6:00pm – 7:00pm
Join us for an inspiring conversation with Abby Phillip, anchor of CNN’s NewsNight with Abby Phillip. In this special event, Phillip will reflect on her journey from her Maryland roots to her remarkable career as a nationally recognized journalist and trusted voice in American media. Guided by moderator Harold T. Fisher, WHUR radio news host, the discussion will offer an inside look at Phillip’s experiences, insights on today’s media landscape, and the lessons learned along the way. Don’t miss this opportunity to hear firsthand from one of journalism’s leading voices in an evening of dialogue, reflection, and connection.
The Vice Napa Valley Wine Dinner
October 13th; Harvest Thyme tavern, Davidsonville 6:30pm
Celebrate the bounty of the season with an unforgettable evening at Harvest Thyme. On Sunday, October 13 at 6:30 PM, enjoy a five-course chef-crafted dinner perfectly paired with bold Napa Valley pours from The Vice winery. Each course is designed to highlight seasonal flavors and elevate your tasting experience. The evening will also feature live music, creating the perfect backdrop for fine food, world-class wine, and great company. Tickets are $135 per person, and reservations are required.
