Photo Courtesy Annapolis Boat Shows
October is Here & We’re Not Easing In…
From powerboats taking over Ego Alley to oyster-fueled festivals, vintage treasure hunts, and yoga breaks that’ll keep you zen between it all—this week is stacked. Think champagne talks with CNN’s Abby Phillip, community walks and rides for a cause, live music that hits every vibe, and markets that will have you shopping like a pro. Clear your schedule, because October’s first week is bringing the energy (and then some). Keep scrolling—your next plan is waiting.
A Conversation with Abby Phillip
October 1st; Maryland Hall for the Creative Arts, Annapolis 6:00pm – 7:00pm
Join CNN’s Abby Phillip, host of News Night, for an engaging conversation on her journey from growing up in Maryland to building a distinguished career in journalism. The discussion will be moderated by WHUR radio news host Harold T. Fisher, offering audiences a chance to hear personal stories, professional insights, and reflections from one of today’s most influential voices in media.
Annapolis Powerboat Show
October 2nd, 3rd, 4th, 5th; Annapolis City Dock, Annapolis
Downtown Annapolis transforms into a boater’s paradise during the Annapolis Powerboat Show, October 2–5. Floating docks line Ego Alley and Annapolis Harbor, creating a temporary marina filled with new and premiering boats, as well as the latest in boating equipment, accessories, and apparel. Whether you’re an experienced boater, an angler, or just starting out, this show offers the perfect opportunity to explore the boating lifestyle, connect with friends, and discover what’s new on the water.
Yin and Peaceful Yoga in Downtown Annapolis
October 2nd; 17 Francis Street, Annapolis 12:00pm – 1:00pm
Take a restorative break with Mid-Day Yoga every Thursday at 12:00 PM. This all-levels guided session offers a calm, welcoming space to stretch, move, and reset in the middle of your day. 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 weekly class helps you relax, recharge, and return to your afternoon feeling centered and energized.
World Is Your Oyster Fest 2025!
October 2nd; B&O Railroad Museum, Baltimore 5:30pm – 9:30pm
Celebrate the Chesapeake Bay’s beloved bivalve at World is Your Oyster Fest on Thursday, October 2, at the B&O Railroad Museum. This lively festival features fresh local oysters, seafood, and handcrafted drinks, plus fun experiences like the Tito’s Handmade Vodka Shucking Competition and “Shuck Like a Pro” lessons. More than just a feast, the event highlights the vital role oysters play in restoring the Bay and honors the community working to protect it. With great food, drinks, and energy, it’s a shell-e-bration you won’t want to miss.
The Local Singer Songwriters Round
October 2nd; Cult Classic Brewing Company, Stevensville 6:30pm – 9:30pm
Back by popular demand, the Local Singer-Songwriters Round returns to Cult Classic Brewing Company on Thursday, October 2. This special evening features an incredible lineup of regional talent, including Elena Barrett, Bobby Hensley, Ashley Chapa, Jen Schimpf, and Nicholas Ray. From soulful country and Americana to indie blues and heartfelt storytelling, each artist brings a unique voice and authentic experiences to the stage. Reserved seats are $10 per person, with doors opening at 6:30 PM and the show beginning at 7:00 PM. Guests can enjoy Cult Classic’s full kitchen, bar, and 15+ beers on tap while experiencing some of the area’s best rising musicians.
100 Women who Care Annapolis
October 2nd; Café Mezzanotte, Severna Park 6:45pm – 8:00pm
Join 100 Women Who Care Annapolis, a giving circle dedicated to supporting local nonprofits through the power of collective impact. Twice a year, members gather, each contributing $100, and vote to direct the combined funds—creating a $10,000 gift for a local organization making a difference in the Annapolis area. It’s simple, powerful, and meaningful: women coming together to support their community in a big way.
Mid-Atlantic Small Craft Festival XLII
October 3rd; Chesapeake Bay Maritime Museum, St. Michaels 10:00am – 5:00pm
The Chesapeake Bay Maritime Museum hosts the 42nd annual Mid-Atlantic Small Craft Festival October 3–5 in St. Michaels. This family-friendly event showcases dozens of traditional and contemporary small craft, including sailing skiffs, rowing shells, kayaks, canoes, and one-of-a-kind boats, many of them on the water. Visitors can explore the craftsmanship behind each vessel, meet boat owners and builders, and enjoy a weekend filled with demonstrations, races on the Miles River, and a People’s Choice competition. Festival hours are 10:00 AM–5:00 PM each day, with general admission valid for two consecutive days.
2025 Every Step Counts Autism Walk & 5k
October 4th; Centennial Park, Ellicott City 9:00am – 12:00pm
Tie up your sneakers and don your best superhero gear for the Autism Society of Maryland’s Every Step Counts Autism Walk & 5K Run on Saturday, October 4, at Centennial Park in Ellicott City. This community favorite brings together the Autism community and allies for a day of fun, connection, and celebration. Participants can run the 5K, walk the 4K, or enjoy a relaxed 1K stroll—all while supporting vital programs and services that benefit thousands of individuals and families across Maryland.
CAC’s 11th Annual Arts in the Park Free Community Festival!
October 4th; Chesapeake Arts Center, Brooklyn Park 10:00am – 3:00pm
Celebrate creativity at the 11th Annual Arts in the Park Free Festival on Saturday, September 20, at the Chesapeake Arts Center in Brooklyn Park. This signature community event draws more than 1,000 residents for a day filled with live entertainment, hands-on art activities, local vendors, delicious food, and family fun. Held in front of CAC’s Hammonds Lane Theatre, the festival features new additions alongside returning favorites, promising the most vibrant celebration yet. Perfect for all ages, it’s a day of art, music, and community you won’t want to miss.
Wanderland
October 4th; Merriweather Park at Symphony Woods, Columbia 11:00am – 4:00pm
Experience a day full of flavor, music, and discovery at A Maryland Craft Journey on Saturday, October 4, at Symphony Woods in Columbia. Presented by the Brewers Association of Maryland in partnership with Hops & Harvest, this immersive festival features tasting zones with 40+ regional craft beverage makers, plus fire-kissed food, artisan vendors, and interactive experiences. Guests can also enjoy live performances from local and national artists on the iconic Chrysalis Stage, making this event a true celebration of Maryland’s creativity and community spirit.
100 Plates Dinner
October 4th; Four Seasons Community Clubhouse, Chester 5:00pm – 9:30pm
Enjoy an elegant evening at the 100 Plates Dinner, a fundraising event in support of Haven Ministries. Guests will savor a beautifully prepared meal while helping raise vital funds for programs that provide shelter, food, clothing, education, and resources to those in need. The evening also features a silent auction with unique experiences, artwork, sports tickets, and more, plus opportunities for sponsorship starting at $250.
Lifeline 100 Bicycle Event
October 5th; Kinder Farm Park, Severna Park 6:00am – 6:00pm
The Lifeline 100 Community Bicycle Event invites riders of all ages, abilities, and bike types to take part in a celebration of cycling and community. Participants can choose from scenic 65- and 100-mile county tours with waterfront views and historic sites, or opt for family-friendly 15- and 30-mile paved trail rides. The event also features a free bike rodeo and fun ride for kids, making it a day for the whole family. Since its start, Lifeline 100 has promoted cycling awareness, safety, and health while raising more than $350,000 for local nonprofits.
Ronald McDonald House of Greater Washington, DC Red Shoe 5K
October 5th; National Harbor Plaza Stage, National Harbor 8:00am – 12:00pm
The Red Shoe 5K is the signature annual fundraiser for Ronald McDonald House Charities of Greater Washington, DC, held at National Harbor. Participants can run the 5K, walk a mile, or cheer on the kids in the fun run, all while supporting families with children in medical treatment. The event also welcomes sponsors and volunteers, offering multiple ways to get involved. This beloved tradition brings the community together for a day of fitness, fun, and meaningful impact.
Annapolis Vintage Market
October 5th; Vintage Vibe Finds, Annapolis 11:00am – 5:00pm
Discover unique treasures at the Annapolis Vintage Market, hosted by Vintage Vibe Finds and Artfully Acquired. Featuring 20+ curated vendors, live music, and a food truck, this outdoor market offers a vibrant mix of vintage finds and local charm. Held rain or shine at 40 Hudson Street, it’s the perfect spot to shop, browse, and enjoy a fun afternoon with friends. Vintage Vibe Finds and Artfully Acquired are also open Thursday–Sunday each week for year-round browsing.
