Annapolis Sailboat Show
October 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
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.
The University of Maryland Center for Environmental Science’s Horn Point Laboratory Open House
October 12th, 11 a.m. to 4 p.m.; Horn Point Laboratory, Cambridge
The University of Maryland Center for Environmental Science’s Horn Point Laboratory invites the public to its annual free Open House on Saturday, October 12, 2024, from 11 a.m. to 4 p.m. This 2024 Open House theme is “Treasure Your Bay.” Visitors will have the opportunity to explore the many reasons to treasure the Chesapeake Bay, including the marine and human life it supports. Horn Point Laboratory’s team of scientists will share their research through fun, interactive exhibits and activities for all ages.
Providence of Maryland's 10th Annual Harvest Bash
October 12th, 7 p.m.; Providence's Greenhouse, Arnold
Join for the biggest event of the year, Providence's 10th Anniversary Harvest Bash at Providence Greenhouses & Gardens! Enjoy an evening filled with live music, dancing, an autumn-inspired menu, open bar, live and silent auctions, raffles, and more. Shop Providence pottery and fall decor, and indulge in special surprises like a s’mores bar, fresh custom donuts and our signature cocktail, The Fall Classic!
The Annapolis Dragon Boat DragonFest
October 13th; Spa Creek
The Annapolis Dragon Boat Club is pleased to present and invite you to the 3rd Annual DragonFest to be held on Sunday October 13th. ADBC, home ported in Annapolis, is the only club in Maryland to seek out and support Breast Cancer survivors. DragonFest occurs during October for this reason. We strive to get as many people in the boats to engage our mission. ADBC, through Dragon boating on Spa Creek, promotes the development of healthy bodies and spirits, supporting recovery from breast cancer and all other cancers, and grows friendships and teamwork. Did you know that close to 6,000 women in Maryland will be diagnosed with breast cancer? 1 in 8. ADBC’s all volunteer band of warriors and others has a lot of work to do and we can’t do it without support.
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.
Spirits of the Past Tour at the William Paca House
October 14th, 11 a.m.; William Paca House and Garden, Annapolis
In October, experience a spirited tour of the historic William Paca House, highlighting tales of the past: sickness, treatments, mourning rituals, and superstitions. You’ll be guided by candlelight on a special tour focusing on the treatment of diseases, medical practices of the women of the era, contributions of the enslaved, local physicians, and mourning rituals for their dearly departed. The tour continues in the physic garden to learn about the medicinal plants and their use during the 18th century and beyond. Period memento mori jewelry from the collection of Ms. Walters, “K. Walters at the Sign of the Gray Horse”, and mourning garb featured!
Pumpkin Patch for the Light House
Thursdays through Sundays through October 27th; St. Martin's Evangelical Lutheran Church, Annapolis
An Annapolis Tradition - every fall organizations from all over Annapolis come together to sell FRESH EASTERN SHORE PUMPKINS to raise funds for The Light House, a homeless prevention and support center. Come play some games, get a photo opp and purchase a PUMPKIN for a PURPOSE!
An Evening with Annapolis Bluegrass
October 16th, 6 p.m.; Historic London Town and Gardens, Edgewater
Gather for an evening with Danny Stewart Jr. and Sarah Larsen and enjoy their traditional bluegrass repertoire with a modern touch. You'll hear their original compositions showcasing harmony singing, guitar playing, high energy fiddle playing, and a few different styles of toe tapping banjo music! Enjoy their bluegrass duo performance under our special events tent on the banks of the South River.
October 17th through 20th; CFG Bank Arena, Baltimore
Disney On Ice is bringing the party to hometowns across the country, and the guest list is jam-packed with audience favorite Disney characters! Mickey, Minnie, Donald, and Goofy have become DJ’s, remixing Disney tunes into colorful stories at this all-new state-of-the-art ice show. Get ready to turn up the fun when Disney On Ice visits CFG Bank Arena from October 17-20, 2024!
Book Discussion: Rivers of the Eastern Shore (Choptank, Miles, and Wye Session)
October 17th, 2 p.m.; Eastern Shore Conservation Center, Easton
Join ShoreRivers for an immersive journey into the history of Maryland's Eastern Shore, as we explore how its rivers shape our way of life then, now, and in the future. We invite you to a special book discussion featuring the second edition of The Rivers of the Eastern Shore by Hulbert Footner, with a forward by Tom Horton.
October 17th, 3 to 7 p.m.; Chestertown YMCA, Chestertown
The 2024 Kent County Community Health and Wellness Expo will be held Thursday, October 17th from 3 – 7 p.m. at the Kent County Family YMCA, 200 Scheeler Road, Chestertown, Maryland. With over 60 vendors, expert speakers, live entertainment, and refreshments, this free event serves to educate and inspire healthy living and wellness for all ages throughout the Kent County community.
Maryland Fall Home & Garden + Craft Show
October 18th, 10 a.m. to 6 p.m.; Maryland State Fairgrounds, Timonium
Get inspiration and expert advice at the annual showcase of everything you need for repairs, renovation, and relaxation. More than 300 exhibitors offer the latest products and ideas for indoor and outdoor spaces, and 100+ crafters have those must-have and sure-to-please items for everyone on your holiday gift list. Sample gourmet treats from three dozen food producers. Meet celebrities Ashley Morrill and Ryan Eldridge of the Maine Cabin Masters TV show and learn about their favorite projects. See live animals in the Fall Fun Zone and learn to play pickleball on the full-size court.
October 19th; Rams Head Live!, Baltimore
Rock 'N' Roll all night with us on Saturday, October 19th for the 21st Annual Rock 'N' Roll Bash at Rams Head Live! Powerplant, Baltimore. The entertainment lineup will feature High Voltage, the nation's premier AC/DC tribute band. They will rock out this year's Bash with a high-energy performance by capturing the pure essence and excitement of a live AC/DC concert! Additional entertainment information coming soon!
October 19th; American Legion Post 91, Cambridge
The next show date is Saturday October 19, 2024, we will be holding the “Fun Dog Show" in the American Legion on Route 50 by the bridge the Choptank River in Cambridge. This event has grown into a local tradition. Registration begins at 9:00 A.M. and begins with a blessing of all dogs and a parade of all dogs and their owners at 10:00. Dogs must be at least 6 months old and on a leash in order to compete. The first category entry is $5.00; additional categories, $4.00 each. A raffle features gift certificates from many local business, and in the past has included the newest American Girl doll, a handmade quilt, and a Lionel train. The event is free to the public. A portion of the proceeds from the event benefit the Baywater Animal Rescue.
October 19th; Pip Moyer Recreation Center, Annapolis
Want to start your holiday shopping early this year? Looking for a piece of furniture or some skis or golf clubs and don't feel like paying top dollar for them? Try the Annapolis Recreation and Parks Rummage Sale on Saturday, October 19 from 8am-12pm. As usual, the Rummage Sale will take place in the parking lot at "Pip" Moyer Recreation Center, 273 Hilltop Lane in Annapolis.
The Wine Festival at Kurtz's Beach
October 19th and 20th; Kurtz's Beach, Pasadena
Surrounded by some of the most beautiful Chesapeake Bay shoreline and centrally located in Maryland, Anne Arundel County is in many ways the heart of our wonderful state. What better way to celebrate a gorgeous day by the Chesapeake Bay than with dozens of area wineries, culinary artists and master artisans? Now in its eighth year, The Wine Festival at Kurtz’s Beach offers a high-end, all-encompassing festival that features a variety of vendors, musicians and attractions.
250TH Anniversary of the Burning of the Peggy Stewart
October 19th, 11 a.m.; Hogshead, Annapolis
A living history experience watching imagery of the Burning of the Peggy Stewart 250 years to the day of the Annapolis Tea Party. View a drone show surrounding a tall ship replicating a colonial era merchant brig where Annapolis City Dock meets the Severn River. Witness the night sky ablaze with a reenactment and commemoration of the revolutionary anniversary.
Annapolis Town Center Fall Fest
October 19th, 11 a.m. to 2 p.m.; Annapolis Town Center, Annapolis
Pick your Own Pumpkin Patch and Decorating, DIY S’mores, Face Painting, Costume Contest, Photo Ops, Live Music, Street Performers, Food Trucks, Vintage Views Mobile Bar. Please consider bringing a canned food or monetary donation to benefit the Anne Arundel County Food Bank!
October 19th; Park Plaza Shopping Center, Severna Park
Don’t miss this fun, FREE, family event! We will have music, shopping, Trick or Treating, a costume contest, a photo booth and more! SHOPTOBERFEST is a Fall Shop Local Festival with a Halloween and Oktoberfest Flair. Exhibitors can sell their products/services at their booths.
Navy Football Home Game vs Charlotte
October 19th, 3:30 p.m.; Navy-Marine Corps Memorial Stadium, Annapolis
Our Mids are taking on Charlotte for the 2024 season's Homecoming. Come support for the only home game of October
October 20th; Downtown Annapolis
We hope you’ll join us for the best day on Maryland Avenue. Enjoy browsing your favorite shops alongside local vendors and makers. Discover vintage finds, candles, art, and handmade goodies. Enjoy live music and performance. Eat, Drink, and be Merry!!
October 21st, 8 a.m.; Renditions Golf Club, Davidsonville
When your child is struggling in school, it can be a frustrating and lonely road trying to figure out the best solution for your child. For 35 years, The Summit School has built an incredible record of encouraging and empowering children with dyslexia and related learning differences become successful readers and learners. All proceeds from Swing for Summit support The Summit School's unique program which incorporates highly trained teachers, evidence-based instruction, hands-on, multi-sensory learning and small class sizes to create transformational experiences for these amazing children.
