Annapolis Power Boat Show
Pumpkin Patch for the Light House
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
October 3rd to October 6th; Annapolis City Docks
October brings the transformation of Ego Alley and Annapolis Harbor into a boater’s dream, as floating docks create a temporary marina showcasing new and premiering boats and the latest in boating accessories, equipment and apparel during the Annapolis Powerboat Show. Whether you are a boater, angler, or just getting started, you will want to grab your family and head to downtown Annapolis and soak in the boating lifestyle, catch up with old boating friends, and make new ones as you walk the docks.
October 3rd; William Paca House & Garden, Annapolis
Spooky season is here! Join us for this special Paint Night at the William Paca House and Garden. Sip a glass of wine (or cider) as our instructor guides you step-by-step in the creation of your own seasonal painting masterpiece. All levels welcome, no experience required!
Mid-Atlantic Small Craft Festival XLI
October 4th through 6th; Chesapeake Bay Maritime Museum, St. Michaels
CBMM will host the Mid-Atlantic Small Craft Festival XLI on Friday-Sunday, Oct. 4-6, welcoming one of the nation’s largest gatherings of small boat enthusiasts and unique watercraft back to its waterfront campus. Hundreds of amateur and professional boatbuilders and enthusiasts will come from all over the region to display their one-of-a-kind kayaks, canoes, and other traditional small craft at the 41th edition of the annual festival, which runs 10am–5pm all three days.
1st Annual Putt for Paws Golf Tournament
October 4th; Chester River Yacht & Country Club, Chestertown
Join us for the Animal Care Shelter for Kent County's first annual golf tournament, to benefit Animal Care Shelter for Kent County!
Annapolis Symphony Orchestra Masterworks Season
October 4th; Maryland Hall, Annapolis
Our tagline for the 2024-2025 season is "Music Matters". Artistic Director and Conductor Maestro José-Luis Novo is dedicated to presenting composers, guest artists, and compositions that make us think, feel, and act. This focus is vital to the ASO's mission to create connections with each other and throughout our community through music.
Children's Theatre of Annapolis Fall Fest
October 4th, 5:30 p.m.; Children's Theatre of Annapolis
Join us as we celebrate the beauty of the season at our annual Fall Festival! Bring your family and friends to enjoy: Family Friendly Haunted House, Face painting and Arts and Crafts, Local Vendors, Food Trucks, Live Music and Open Mic, and Seasonal treats and more!
October 5th; Luminis Health, Annapolis
In honor of Breast Cancer Awareness Month, Luminis Health Doctors Community Medical Center is hosting its annual Pink Ribbon Rally Saturday, October 5 on our Lanham campus. The event aims to spotlight the importance of breast cancer awareness and the crucial role of early detection through mammograms. The Pink Ribbon Rally will feature no cost mammograms and clinical breast screenings, as well as life-saving information about the signs, symptoms, and early detection of breast cancer.
October 5th; Bowie Baysox Stadium
Award-winning Tacos & Tequila Music Fest is coming to Bowie! Get ready for a night of incredible throwbacks, great food, and, of course, LOTS of Tequila!
October 5th; Annapolis Town Center
Ready to raise the woof? Join us and Peake Social for the second Barktoberfest for plenty of steins and canines as we celebrate German-style beer, bavarian food, and pawesome four-legged friends. Returning is the crowd favorite dog fashion/costume show, imported and locally crafted brews, and yard games. A portion of the proceeds will go directly to the Anne Arundel SPCA! Expect additional traditional Oktoberfest fun with stein-holding contests and plenty of fall photo opportunities. General admission will be held at the Annapolis Town Center at the Boathouse Pavilion in the East Village. Don’t miss out! Dogs that are friendly and on a leash are welcome but should be comfortable with crowds and other dogs nearby.
October 5th; Sultana Education Foundation's Bay Studies Center, Chestertown
Join us for an old-fashioned harvest fest at Sultana’s new Lawrence Wetlands Preserve in Chestertown. Bring a blanket, bring the family, and spend a few hours surrounded by nature as you enjoy great music, food, friends, and drink. Did we mention there will be plenty to do for the kids?
October 5th; Chesapeake Bay Environmental Center, Grasonville
The Chesapeake Bay Environmental (CBEC) in Grasonville, MD is a 501c3 non-profit organization whose mission focuses on education, research, conservation, and habitat restoration. We are excited to bring you the Annual CBEC Little Bobbers Fishing Derby which will not only raise funds for creating fishing reefs and oyster beds at CBEC but also introduce kids to the hobby of fishing and all the fun that goes with catching the big one!
October 5th; Downtown Rock Hall
Rock Hall FallFest pays homage to the almighty oyster by inviting guests to savor oyster stew and fried oysters while browsing dozens of artisan and craft booths. While the oyster is the star of the show, this festival features all the highlights of Kent County, including a variety of live music performances, children’s activities, and the opportunity to explore beautiful Rock Hall, Maryland.
October 5th, 9 a.m.; Odenton Volunteer Fire House, Odenton
Come out for a day of free fun, food, and learning with Odenton Day 2024. It runs from 9 a.m. to 2 p.m. a the Odenton Volunteer Fire Department. The day will include the fire company's open house, fun activities for kids, hot dogs, chips, drinks, music and entertainment
Chesapeake Arts Center's 10th Annual Arts in the Park
October 5th; Chesapeake Art Center, Brooklyn Park
Celebrate the 10th anniversary of Chesapeake Arts Center’s (CAC) Arts in the Park Free Festival! This milestone event will bring together over 1,000 local residents, art enthusiasts, and community organizations for a day of vibrant entertainment, delicious food, interactive art activities, stunning art displays, and exciting giveaways.
Higgins Pet Fair & Crofton Dog Show
October 5th; Crofton Country Club
There will be pet related vendors, animal rescues and demonstrations., a fun dog show with classes including best costume, most tricks, and a pie eating contest. This is a benefit for Rude Ranch Animal Rescue and the Spay Spa/Neuter Nook (spay/neuter clinic). There will be pet related vendors, animal rescues and demonstrations. There will also be a fun dog show with classes including best costume, most tricks and a pie eating contest.
District I's nine Eastern Shore Garden Club's Patriotic Standard Flower Show
October 5th, 1 to 4 p.m.; Elks Lodge, Easton
District I’s nine Eastern Shore Garden Clubs will stage a National Garden Clubs, Inc. (NGC) PATRIOTIC STANDARD FLOWER SHOW at the Elks Lodge #1622 at 502 Dutchman’s Lane in Easton, MD 21601 on Saturday, October 5 from 1 to 4 pm. The public is invited to stroll through and enjoy this colorful free event.
October 5th, 4 p.m.; Maryland Therapeutic Riding, Crownsville
Don your cowboy boots and join us for a boot-scootin' good time for Hoedown on the Farm at Maryland Therapeutic Riding. The family-friendly Hoedown on the Farm is back and to celebrate 28 years of the healing power of horses! Come enjoy live music from Mark Bray and the Steel Soul Cowboys, fun games and activities (including a mechanical bull!), BBQ from Adam's Taphouse Grille, and a chance to win some great raffle prizes...including a 50/50 Raffle.
2024 Lifeline 100: Scenic Rivers' Ride for Land & Water
October 6th; Kinder Farm Park, Millersville
Scenic Rivers Land Trust is pleased to once again be an official nonprofit partner for the 2024 Anne Arundel County Lifeline 100 Century Ride. We are recruiting cyclists of all ages and abilities to take part in this unique, organized ride of our beautiful county and raise funds on our behalf. The Anne Arundel County Lifeline 100 Century Ride offers a great experience for cyclists of all levels with 100, 65, 30, and 15 mile route options as well as a family fun ride. These routes wind throughout scenic Anne Arundel County including views of downtown Annapolis, the Severn River, southern Anne Arundel County, and more!
AA County Sheriff 5K Fall Festival
October 6th, 8 a.m.; Anne Arundel County Fairgrounds, Crownsville
The fall festival benefits Chesapeake K9 Fund with beer trucks, live music, food trucks vendors and more.
October 6th; Town of Centreville
Our Porch Party is a community event with live music and food trucks. From 2-6 pm, performances will take place on the beautiful porches and historic buildings of downtown Centreville, including the lawn of St. Paul’s Church. Musical genres have been selected to draw a diverse audience: jazz, blues, party rock, country rock, contemporary, Latin, and orchestral sounds, with a rhythm and blues grand finale on the Courthouse Square.
October 6th; Riva
This 5 Mile event celebrates the awesomeness of outdoor recreation on the South River and supports the efforts of Live Water Foundation and Arundel Rivers Federation! We are a gathering of novice and experienced swimmers & paddlers celebrating the efforts of these organizations and the impact they have on inclusive water access and sustainable rivers. Each participant is required to fundraise at least $100 in addition to their registration fee. The tools to help you reach the fundraising goal will be provided. Fundraisers who exceed $500 will have their registration fee reimbursed.
October 6th; West Street, Annapolis
Inner West Street Association is the proud sponsor of Maryland's premier art festival. From May through November, thousands of visitors enjoy shopping along beautiful West Street in downtown historic Annapolis.
October 8th, 6 p.m.; Harris Crab House, Chester
Crabs for a Cure is benefitting Bosom Buddies Charities with a crab and oyster feast featuring steamed crabs, oysters, buffet, draft beer and sodas!
October 8th; Crofton Country Club, Crofton
Indulge your taste buds with a diverse array of cuisines at Taste of Crofton. From savory appetizers to delectable desserts, there’s something for everyone to enjoy. Discover new favorites and support local businesses all in one evening. Eat. Socialize. Enjoy. Celebrate Crofton’s 60th Anniversary!
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.
True Colors: Mental Health Awareness Art Show
October 8th through October 12th; Todd Performing Arts Center, Wye Mills
Crossroads Community, Inc. and Corsica River Mental Health Services, Inc. are excited to announce the 5th annual "True Colors" Mental Health Awareness Art Show. We invite artists from the Eastern Shore community and beyond to participate. The show will be held at the Todd Performing Arts Center at Chesapeake College from October 8 to October 12, 2024, in celebration of Mental Health Awareness Week. A reception will take place on October 11, from 4 PM to 7 PM, with free admission, live music, and light refreshments for all attendees.
October 10th through October 14th; Annapolis City Docks
This annual celebration of sailing features floating docks lined with sailboats from manufacturers around the world. Multihulls, monohulls, cruisers, racers, sailing dinghies and more. Show tents line the shore, stocked with the latest in nautical gear and accessories, electronics, communication equipment, sails, rigging, education, charter companies, clubs and more.
Anne Arundel County Hispanic Heritage Awards
October 10th; Live! Casino & Hotel, Hanover
Welcome to the Anne Arundel County Hispanic Heritage Awards Ceremony! Join us on Thu Oct 10 2024 at 5:30 PM at Live! Casino & Hotel Maryland to celebrate the outstanding contributions of the Hispanic/Latino community in our county. This in-person event will be a night filled with recognition, cultural performances, and delicious food. Come and show your support for our Latino neighbors and friends. Don't miss out on this special evening honoring the diversity and richness of our community!
Annapolis Chapter Annual Fundraising Banquet
October 10th; Chesapeake Bay Foundation, Annapolis
The Annapolis Chapter of Coastal Conservation Association (CCA) Maryland welcomes you to join us for a celebration of conservation, and all things Chesapeake Bay. As a recreational fishing based organization, we know that the public’s connection to the Chesapeake Bay through fishing and boating is what drives the passion to ensure that future generations will also enjoy what is so near and dear to us. This fundraising dinner directly supports CCA Maryland’s focus on ensuring the health of our marine resources and anglers access to them, and our objective to conserve, promote and enhance our marine resources for the benefit of the general public.
October 12th; Downtown Cambridge
Taste of Cambridge returns for its 16th year on Saturday, October 12, from 12pm to 6pm. Celebrate the best of Eastern Shore cuisine with Cambridge Main Street’s premiere community street festival.
October 12th, 10 a.m. to 4 p.m.; Quiet Waters Park, Annapolis
Celebrate the 34th year of Art @ the Park. The show is set in the beautiful Quiet Waters Park, in Annapolis, Md. The Arts Festival is a great gathering of live music, a wide variety of visual arts and Food! The event is held on Saturday, October 12th and Sunday, October 13th from 10-4 each day. The arts festival is one of the best family friendly activities available. There are live demonstrations, free children's activities, live music and art set in the most stunning park in Anne Arundel County. The gate fee is a meager $6 per car. Your pets are welcome in the outdoor areas.
October 12th, 11 a.m. to 3 p.m.; Adkins Arboretum, Ridgely
Join us for an enchanted day outside full of maypole dancing, magical potions, elven archery, artisan fairy houses, a meadow pirate ship, and more. Live entertainment all day; refreshments available for purchase from Beltway Bistro, Blue Monkey, and Night Kitchen Coffee and Bakery. Don’t forget your fantastical costumes and a camera for photos with the Fairy Court!
October 12th, 12 to 4 p.m.; Easton Volunteer Fire Department, Easton
The 9th Annual Craft Beer Fest will be held on Saturday, October 12, 2024 from Noon to 4pm (VIP’s Enter at 11am). Maryland’s largest under cover craft beer festival will feature 40+ Breweries, Wineries and Distilleries will be pouring 120+ Craft Beers, Ciders, Seltzers, Wines & Spirits from the Mid-Atlantic region and beyond, with Live Music. Food, Vendors, Raffles and games of chance will be available. MUST BE 21+ TO Attend (ID required to enter) For more information go to https://eastonbeerfest.com/
Captain Avery Museum's Oyster Festival
October 12th, 12:30 to 5 p.m.; Captain Avery Museum, Shady Side
Captain Avery Museum, with our generous sponsor Nugent Design Build, presents the 27th annual Oyster Festival. Come out for fine company, live music, a cash raffle, local food and the best oysters anywhere! Fresh oysters raw or steamed and shucked in front of you by the Anne Arundel County Watermen's Association. Skipper’s Pier will serve food from their renowned menu, and Chesapeake Grille will have its popular crab soup, as well as burgers, and hotdogs.
Chestertown Challenge Half Marathon & 5K Run/Walk
October 13th, 9 a.m.; Wilmer Park, Chestertown
Both courses USAFT certified. Race day registration will be available! Packet pickup starts at 8 a.m. and races start at 9 a.m. at Wilmer Park, Chestertown, MD. 5K Run/Walk – $25 before September 22, $30 after. Half Marathon – $50 before September 22, $60 after.
