A list of our favorite local events for the month of October. Event dates may be subject to change due to COVID restrictions.
United States Powerboat and Sailboat Shows
The United States Boat Shows are back this October in Annapolis. The United States Powerboat Show will take place October 7th through 10th at the Annapolis City Docks, while the United States Sailboat Show will follow October 14th through 18th. This internationally acclaimed sailboat show is recognized as the world’s largest and most prestigious show of its kind. Find more information at annapolisboatshows.com.
Photo by Jamie-Leigh Bissett, OffbeatPhotographer.
Providence Center’s 60th Anniversary Harvest Bash
Visit Providence Center Greenhouse & Gardens in Arnold on October 16th at 6 p.m. for the 60th Anniversary Harvest Bash. Not ready to go to the Bash quite yet? Not a problem. Sign up to receive the At Home Experience Box and participate in the virtual Bash. Details at providencecenter.com.
Photo by Ken Tom
Blazers. Bourbon. Cigars.
Historic Annapolis’ Blazers. Bourbon. Cigars. is back on October 21st from 6 to 9 p.m. at William Paca House and Garden. Spend the evening networking with fellow businessmen and community leaders. Enjoy bourbon, whiskey, and other fine liquor tastings, along with cigars, delightful food from the area’s top chefs, and an array of vendors. All proceeds benefit Historic Annapolis. Find more information at annapolis.org.
2021 International Edgar Allan Poe Festival & Awards
Gather at the Edgar Allan Poe House & Museum and Poe Park on October 2nd & 3rd to commemorate the 172nd anniversary of Edgar Allan Poe’s death and for a Death Weekend Poe Places Tour. The fourth annual event is free and will feature Poe-themed performances, art, vendors, food, and more to celebrate Poe’s life, works, and influence on the arts. Full information at poefestinternational.com.
Fourth Annual Mental Health Gala and Awards Ceremony
On October 2nd, from 6 to 10 p.m., the National Alliance on Mental Illness of Anne Arundel County will be hosting their Fourth Annual Mental Health Gala & Awards Dinner. Join in being a beacon of hope to families living with mental illness by attending the ceremony at Crowne Plaza Hotel in Annapolis. For more information, visit namiaac.org.
Hops & Harvest Festival
Gather at Merriweather Park at Symphony Woods in Columbia on October 2nd for the Hops & Harvest Festival. Tickets include unlimited tastings, live entertainment, games, and so much more. Beer, wine, and spirits will be provided from breweries, distilleries, and wineries all over Maryland and entertainment from Kelly Bell Band, DJ Chris Tharp, Miss Moon Rising and more. Find more information at hopsandharvestfest.com.
Halloween Party and Parade
Whoof on the Wharf is having a Halloween Party and Parade in Edgewater on October 30th at 2 p.m. Be ready for all of the Halloween fun with witches, werewolves, and whatever we see paddling down the South River. They will have a costume contest, paddling parade, professional photos and more. Find more information on their Facebook page.
13th Annual Calvert Arts Festival
Six wineries will be featured at the 13th Annual Calvert Arts Festival on October 9th from 10 a.m. to 5 p.m. at All Saints Episcopal Church in Sunderland. Shopping the local venues is free and a $15 fee will enable you to taste wines and beers with a souvenir tasting glass. There will be live entertainment, food, crafts, raffles, and plenty more. More information at allsaints1692.org.
Photo by Martin Image Photography
4th Annual Run for the Dogs in Blue 5K Run/1 Mile Walk
On Sunday, October 24th, at 7:30 a.m. at Quiet Waters Park, run a 5K or walk a mile to support the Chesapeake K-9 Fund. This is a family and dog friendly event and each participant will receive an Under Armour Race Shirt and a Medal. After the race there will be a live K-9 demonstration. Buy your tickets now at Whatsuptix.com.
49th Annual Independent School Fair 2021
Black Student Fund and Latino Student Fund is hosting their School Fair on October 17th from 2 to 5 p.m. at Walter E. Washington Convention Center in Washington D.C. This event is a forum for families to learn more about independent school education and engage students, teachers, and administrators from more than 70 local and national independent schools and educational programs. Search eventbrite.com for details.
GiGi’s Playhouse Golf Outing
On October 13th at The Cannon Club in Lothian, GiGi’s Playhouse will be having their 2nd Annual Golf Outing. The golf package will include breakfast, lunch, and post-game appetizers, beverages all day on the course, greens and cart fees, 50/50 drawing and raffles, and more. All proceeds will benefit GiGi’s Playhouse in Annapolis. For more information, visit gigisplayhouse.org/Annapolis.
Quiet Water’s 31st Annual Art and Music Festival
Quiet Water’s Park in Annapolis is having their 31st Annual Art and Music Festival featuring original artwork, demonstrations, music, and specialty food trucks on October 16th and 17th. The festival be 10 a.m. to 6 p.m. and the fee is $6 per car. Search for details at aacounty.org/departments/recreation-parks.
FairyFest
Bring your wings to Adkins Arboretum on October 9th from 11 a.m. to 3 p.m. for a full day of magic. Follow a trail of fairy houses along enchanted forest paths, hung for gnomes in Emily’s Play Garden, and join in a meadow maypole dance. There will be live entertainment, magical games, crafts, and even a pirate ship. More details at adkinsarboretum.org.
Founder’s Day Hoedown
Get your cowboy boots ready for a boot scootin’ good time to celebrate the 25th Anniversary of Maryland Therapeutic Riding. MTR works with the natural healing and therapeutic power of horses to improve the quality of life of individuals faced with all kinds of challenges, whether they are physical, cognitive, mental, or emotional. The hoedown will take place October 9th from 6 to 10 p.m. at 1141 Sunrise Beach Road in Crownsville. There will be live music by Mark Bray & The Steel Soul Cowboys and dinner catered by Adam’s Taphouse & Grille. Event details at horsesthatheal.org.
Sultana Downrigging Festival
Sultana Downrigging Festival is coming back to Chestertown October 29th through 31st. Sultana Education Foundation has hosted this event for 21 years now and it is one of the largest annual tall ship gatherings in North America. The festival will feature Tall Ship sails, tours, incredible live bluegrass music, lectures, exhibits, family activities, regional food, and more. Find more information at downrigging.org.
Chesapeake Film Festival
Chesapeake Film Festival is back, live and in-person October 1st and 2nd and being presented virtually October 3rd through 10th. The excitement of watching films on the big screen is back. The in-person viewings will be shown at Easton’s Avalon Theatre and the virtual showings can be found at chesapeakefilmfestival.com. Nearly 60 films will be shown in total including documentaries, animation, shorts, narratives, student films, Made in Maryland films, thrillers, and environmental films.
Easton Beer Fest
Drink local at Easton’s 6th Annual Beer Fest on October 2nd from noon to 4 p.m. The event will be hosted by and supporting the Easton Volunteer Fire Department and will continue to be the largest indoor craft beer festival in Maryland. The festival will feature 40-plus breweries and craft beers from the mid-Atlantic and beyond as well as music, food, vendors, raffles, and plenty of games. Find more information at discovereaston.com.
OysterFest
Sip, slurp, and savor at Chesapeake Bay Maritime Museum’s OysterFest on October 30th, in St. Michaels. The festival will feature oysters served in a variety of ways, other local fare, craft beer and spirits, live music, and scenic river cruises aboard Winnie Estelle and so much more. Local chefs will feature their own signature oyster dishes throughout the day, so be sure to try them all. Find more information at cbmm.org.
Rock Hall Fall Fest
Celebrate our Eastern Shore Heritage with family and friends at Rock Hall’s Fall Fest. The festival will take place October 9th in Downtown Rock Hall. This event attracts thousands of visitors from across the Eastern seaboard showcasing the quaint hamlet of Rock Hall. This festival will feature music, local oysters, over 40 handicraft vendors and plenty of activities for children. Visit rockhallfallfest.org for details.
Academy Art Museum Annual Craft Show: Bridging Fine Craft & Community
Academy Art Museum’s 24th Annual Craft Show is back October 15th through 17th. See work from over 50 artists from across the United States. The show will take place at Academy Art Museum in Easton and is the cultural hub of the Delmarva region for art and educational programming. All proceeds from ticket fees and generous community sponsorships go directly to support the Museum’s mission of providing meaningful art experiences and education to the Mid-Shore. Find more information at academycraftshow.com.