Photo courtesy of Annapolis Boat Shows
GiGi's Playhouse Annapolis Golf Outing
October 5th; Queenstown Harbor
All proceeds benefit GiGi’s Playhouse Annapolis, a nonprofit organization with a mission to change the way the world views Down syndrome. The golf package includes breakfast and lunch, a 50/50 drawing, custom golf towel and more!
October 5th through 8th; 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.
Pumpkin Patch for The Light House
October 5th through October 28th; St. Martin's Evangelical Lutheran Church, Annapolis
An Annapolis Tradition! Each October, the Friends of the Light House teams up with volunteers from local churches and synagogues to host our fun Pumpkin Patch at St. Martin’s Lutheran Church on Spa Road. Come find your perfect pumpkin sourced locally from the Eastern Shore and support our beloved Light House at the same time!
Greater Chesapeake Bay Schooner Race Watch Party
October 5th, 11 a.m. to 2 p.m.; Annapolis Maritime Museum
Bring you camera and join us aboard the historic skipjack, Wilma Lee for The Great Chesapeake Bay Schooner Race Watch Party! Come see the start of the 130-mile race from Annapolis to Norfolk Virginia. Tickets include drinks and a complimentary lunch from Bread and Butter. 21+
Academy Art Museum Outdoor Movie Night
October 6th; Academy Art Museum, Easton
Families are invited to come early, bring a picnic, and enjoy a free art project sponsored by The 911 Day of Service Project/Americorps. Please note: Movies begin around 8:00 PM (when it is fully dark outside)
Easton's First Friday Gallery Walk
October 6th; Downtown Easton
On First Friday the art galleries of downtown Easton extend their hours and invite you on a tour of artistic adventure! View new art exhibits, meet the artists, and discover sales and great deals!
Fall Kick Off at Avalon Theatre
October 6th and 7th; Avalon Theatre, Easton
The Fall Kick-Off weekend is a time to celebrate our outdoor beauty, while our indoor activities are heating up! This year the weekend will include: Giant Pumpkin Carving, Easton Brew Fest- get your tickets Here!, Outdoor Live Music, Tablescape Competition , Tasting Room, First Friday Gallery Walk, Outdoor Movie Night at the Academy Art Museum
Mid-Atlantic Small Craft Festival
October 6th through 8th; Chesapeake Bay Maritime Museum, St Michaels
Hundreds of amateur and professional boat builders, model boat builders and enthusiasts come from all over the region to display their skiffs, kayaks and canoes. Watch many of these one-of-a-kind vessels race along the Miles River along CBMM’s 18-acre waterfront campus.
October 6th, 5 p.m.; Crumpton Volunteer Fire Department
We invite you to join us at Crumpton Volunteer Fire Department for Our Food Truck Night…. Lots of delicious food to chose from. Hope to see you there
Tribe Cycle's 5 Year Anniversary Party
October 6th, 5:30 p.m.; Tribe Cycle, Annapolis
Get ready to party because Tribe Cycle is celebrating its incredible 5-Year Anniversary right in their own parking lot on Friday, October 6th! They're kicking off the evening with a high-energy all-Instructor ride from 5:30 PM to 6:30 PM. Mark your calendars because bike bookings open at noon on Friday, September 29th, and you won't want to miss this! www.tribecycle.com 443-808-1234
Broadway in Annapolis: They're Playing Our Song
October 6th, 8 to 10 p.m.; Maryland Hall, Annapolis
What could possibly go wrong when an established songwriter and an up-and-coming lyricist fall in love while they’re writing music together? Find out in this wickedly funny and timeless musical from Tony Award-winners Marvin Hamlisch and Neil Simon! Don’t miss the limited local run of They’re Playing Our Song.
October 7th; Easton Volunteer Fire Department
The 8th Annual Craft Beer Fest will be held on Saturday, October 7, 2023 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)
October 7th; Main Street Chestertown
Your favorite annual car show is back! Enter your car to be judged or come view over 100 antique, classic, and modern cars on display in downtown Chestertown. Live band, food, and more. This event is free and open to the public. All proceeds benefit Main Street Chestertown.
Suburban Maryland Fall Home Show
October 7th through 8th; Howard County Fairgrounds, West Friendship
Our events feature a wide selection of home improvement professionals in a fun, interactive environment. After meeting with and comparing our expert exhibitors, we know you'll be inspired and motivated to start planning with confidence. More importantly, we want you to be excited for all the fantastic possibilities that come with your project!
October 7th; MD Corn Maze, Gambrills
For more than 100 years, the Dairy Farm supplied milk to the Naval Academy midshipmen right here at the farm. Since 2006, our farmers have been growing the corn maze and caring for the farm's grass fed beef cattle and dairy calves for organic milk production. Our friends, The Stolftus family, joined us in 2021, growing all of our pumpkins, gourds and mums locally at their Amish farm in Taneytown, MD. They deliver them weekly in the Fall along with their daughter's homemade whoopie pies so that we can bring you more Maryland farm goodness! As the largest farm parcel left in Anne Arundel County, our family delights in sharing the fun of getting lost in the farm life each Fall season... we love growing memories with you!
October 7th, 9 a.m.; Centennial Park, Ellicott City
Each year, the Autism Society of Howard County’s Every Step Counts Autism Walk & 5K Run brings together those touched by Autism and members of the wider community in a supportive, energizing, and fun environment. This year’s event on October 7, 2023 at 9:00am continues that tradition, featuring a 5K run and a 4K walk around Centennial Lake in Ellicott City, MD, with the option of a more mellow 1K stroll. Attendees can take in the family-friendly Event Village that includes inflatables, entertainment byroving circus performers, bubble and balloon artists, and costumed characters! Registration is now open and includes virtual and non-binary options plus great prizes for top teams and runners. All proceeds benefit the Autism Society, now serving communities in and around Howard, Montgomery and Anne Arundel Counties.
Sudlersville Volunteer Fire Department Fall Vendor & Craft Show
October 7th, 9 a.m. to 2 p.m.; Sudlersville Volunteer Fire Company
SVFC is bringing back their Craft Show for 2023! Mark your calendar for Saturday October 7, 2023 and keep an eye on SVFC social media for more details. VENDORS- Contact Hope Brown (410-443-6820) to reserve your space!
3rd Annual Kent County Touch A Truck
October 7th, 10 a.m. to 2 p.m.; Kent Agricultural Center, Chestertown
A hands on, family-friendly event where you can explore different vehicles and machines, meet community helpers, games, activities, demonstrations, and more! Food will be available for purchase.
October 7th, 10 a.m. to 4 p.m.; Tuckahoe Equestrian Center, Queen Anne
Enjoy Multi Discipline demonstrations like hunter/jumpers drill teams, western pleasure dressage, driving jousting, barrel racing trick riding and more.
October 7th, 10 a.m. to 3 p.m.; Trinity Cathedral, Easton
The Easton Fall Craft Fair will run from 10 am until 3 pm on Saturday, October 7, 2023. Admission is free. It features 35+ artisans from Maryland, Virginia, Delaware and Pennsylvania selling handmade products of all kinds--jewelry, woodworking, ceramics, photography, needlework, embroidery, and much more. Plenty of food and fun!
October 7th, 10 a.m. to 4 p.m.; Homestead Gardens, Davidsonville
Join us for Fall Festival Weekends at Homestead Gardens. Give your family the same enchanting experiences you had as a child; seeing the barnyard animals, taking hay rides, picking out pumpkins and connecting with the community. Create new traditions and make unforgettable family memories.
October 7th, 11 a.m. to 5 p.m.; 12th Street and Chestnut Ave to Maple Ave at 9th Street, Bowie
With its strong ties to the railroad, Old Bowie established itself as a growing vibrant community. Over time, our city became home to people from an ever-growing collection of cultures. Our community invites you to our festival for a day-long celebration.
October 7th, 4 to 8:30 p.m.; Maryland Therapeutic Riding, Crownsville
Join us for a family-friendly event on the farm that includes games, activities, food from Adam's Grille and live music featuring Mark Bray & The Steel Cowboys! All proceeds from the event will support the programs and participants of Maryland Therapeutic Riding.
2023 Black White & Silver Ball for Annual Bill Sweeney Charity Gala
October 7th, 6 p.m.; Blackwall Barn & Lodge, Gambrills
We can't wait to celebrate Bill's legacy, the last year of work done in our community for perinatal support & wellbeing, and honor the angels we have lost along the way. Join us for a night of delicious food & drinks, dancing, stellar auction items, and a whole lot of fun! Forward this message to your friends & family, and save your seat today.
October 8th, 8:30 a.m.; Westfield Annapolis Mall
Westfield Annapolis and The National Ovarian Cancer Coalition (NOCC) are partnering to host the annual TEAL Walk on Sunday, October 8 at 8:30am. This family-friendly event is an important day that brings together a dedicated community united in the mission of saving lives through the prevention and cure of ovarian cancer. The event celebrates survivors, honors those we have lost and brings awareness to this important cause.
Chestertown Challenge Half Marathon & 5K Run/Walk
October 8th, 9 a.m.; Wilmer Park, Chestertown
Half Marathon & 5K Run/Walk to benefit KART, providing therapeutic horseback riding and equine activities for the special needs community. Both courses are 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.
Hands-On History day at the Museum of Historic Annapolis
October 8th, 11 a.m. to 2 p.m.; Historic Annapolis Museum
Visit the Museum of Historic Annapolis on the second Sunday of every month for Hands-On History Days. Drop in any time during event hours for special family activities – a new theme each month means you and your family will want to visit again and again! Activities are included with Museum admission.
October 8th, 12 to 3 p.m.; William Paca House, Annapolis
Drop in and visit the William Paca Garden, a charming respite in the heart of bustling Annapolis. On this day, you’ll encounter the gentry of Annapolis enjoying a garden party, portrayed by the Annapolis Living Historians. Interact with these finely-dressed friends of William & Mary Paca and learn about the foods that were prepared to entertain their distinguished guests in the idyllic garden setting.
24th Annual Sabres Athletic Association Golf Tournament
October 9th, 10 a.m. to 6 p.m.; Talbot Country Club, Easton
On behalf of the Saints Peter & Paul School and the Sabres Athletic Association, we are excited to announce our 24th Annual SAA Golf Tournament! This event will take place on Monday, October 9, 2023 at the Talbot Country Club in Easton, MD. This event has been successful in raising money for the Sabres Program year-after-year and we know this year will be no exception. Thank you to all who have previously participated and we hope to see you again along with some new faces!
Through October 8th; Easton
Save the dates! The 2023 Chesapeake Film Festival (CFF) will be LIVE Sept. 30 and Oct. 1 at two historic venues in Easton, MD. The Festival goes VIRTUAL October 2 through 8, bringing you more fabulous films to watch anytime, anywhere.
The hybrid festival begins with a LIVE weekend (Sept. 30 and Oct. 1) featuring screenings, discussions, events at the Avalon Theatre and Ebenezer Theatre, as well as an Opening Day VIP Reception at the Academy Art Museum. As viewers take their seats in these beautifully restored venues, they are transported into the glory days of theatre.
The VIRTUAL Festival (Oct. 2-8), which follows the LIVE Festival, gives film lovers another week of outstanding films to watch at their convenience. Viewers can view films from a variety of genres including narratives, documentaries, and animations. Take five minutes to watch a pithy short film or grab some popcorn and treat yourself to a fabulous full-length feature.
