Out on the Towne Event Picks for October 2023

A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of October. Event dates may be subject to change.

Annapolis Sailboat Show

One of the most exciting events of the year is back at the Annapolis City Docks from October 12th to 15th. Sailors from around the globe will gather in our capital city to celebrate all things sailing. Floating docks will be lined with sailboats from manufacturers around the world and include multihulls, monohulls, cruisers, racers, sailing dinghies, and more. Find more information and get tickets to the event at annapolisboatshows.com.

Annapolis Powerboat Show

Every October, Ego Alley and Annapolis Harbor is transformed into a boater’s dream. Floating docks at the Annapolis City Docks will create a temporary marina showcasing new and premiering boats and the latest in boating accessories, equipment, and apparel during the Annapolis Powerboat Show. Soak in the boaters lifestyle October 5th through 8th while you walk the docks. Find more information and get tickets at annapolisboatshows.com.

Dragonfest Raffle & Party

Annapolis Dragon Boat Club is hosting their 2nd annual Dragonfest Raffle and Party on October 14th from noon to 4 p.m. for the public. Join the party at Pier 4 Marina in Eastport for live music, a mega raffle, silent auction, wine pull, bbq, oysters, and more. All proceeds from the event will go directly to improving the lives of breast cancer survivors, their families, and friends. Find more information at annapolisdragonboatclub.org.

Eastport Oyster Boys

Anne Arundel Community Concert Association is bringing back the Eastport Oyster Boys at Severna Park High School on October 4th at 7:30 p.m. This lively group is a living legend in our Chesapeake Bay community. You may have seen and heard them at one or another local event. This concert opens AACCA’s season with an upbeat performance of catchy sea tunes and more. Find more information at aaccaconcerts.com.

Bountiful Harvest

Pull out your boots and bling for Friends of The Light House’s 2023 Bountiful Harvest. The harvest will be Friday, October 20th at The Atreeum at Soaring Timbers in Annapolis. Enjoy gourmet food by The Light House Bistro, an open bar, live and silent auctions, and live music by Misspent Youth all while raising money for safe housing and job training for the homeless. Find more information at friendslhs.org.

Hoedown on the Farm

Maryland Therapeutic Riding’s Hoedown on the Farm will be October 7th from 4 to 8:30 p.m. at their campus in Crownsville. Grab your cowboy boots and enjoy a boot-scootin’ good time. Celebrate 27 years of the healing power of horses with live music, games, food, and raffles. Find more information at horsesthatheal.org.

Harvest Bash

Providence of Maryland’s 8th Annual Harvest Bash will be a night like no other on October 14th in Providence’s Greenhouse in Arnold. The night will have a feast of fall bounty and abundant cocktails, custom donuts, live and silent auctions, and live music by The Dan Haas Band and other musicians. Find more information at providenceofmaryland.org.

Old Bowie Festival

Old Bowie’s annual festival is back to celebrate all things Bowie. Over time, the city has become home to people from an ever-growing collection of cultures. Enjoy the day-long celebration on October 7th from 11 a.m. to 5 p.m. The festival will take place between 12th Street and Chestnut Avenue to Maple Avenue at 9th Street in Bowie. The festival will have live music, stages, local and ethnic offerings, and more. Find more information at oldbowiecelebrates.us. 

Lifeline 100 Bicycle Event

Kick off October with Anne Arundel Department of Recreation & Parks, Anne Arundel County Police, and Bicycle Advocates for Annapolis and Anne Arundel County’s ninth Lifeline 100 Community Bicycle Event. The award-winning event offers scenic 65- and 100-mile county tours with water views and historic sites, 15- and 30-mile flat, paved trail rides, and a free bike rodeo and family fun ride for children. The race will start at 6:30 a.m. at Kinder Farm Park in Millersville. Find more information at lifeline100.com.

Suburban Maryland Fall Home Show

The Suburban Maryland Fall Home Show will be held at the Howard County Fairgrounds on October 7th and 8th. The home show’s goal is to inspire, motivate, and excite you for your upcoming home improvements—whether it’s a minor renovation or a major remodel. The event will have a wide selection of home improvement professionals in a fun and interactive environment. The show will have a department for kitchens, bathrooms, landscaping, siding, doors, insulation, and more. Ready to get motivated for your next project? Find more information at mdhomeshows-hf.com.

Sultana Downrigging

The 23rd Sultana Education Foundation’s Downrigging Weekend Festival is one of the largest annual tall ship gatherings in North America and will be back in Chestertown October 27th through 29th. The festival weekend will have sails, tours, live bluegrass music, lectures, food, and more to benefit the Foundation’s environmental literacy programs and the other nonprofits participating in the festival. Find more information at downrigging.org.

Mid-Atlantic Small Craft Festival

The Chesapeake Bay Maritime Museum hosts the 40th edition of the Mid-Atlantic Small Craft Festival Friday, October 6th through Sunday, the 8th, 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 traditional small craft at the festival, which runs 10 a.m. to 5 p.m. all three days. Festival entry is included with CBMM’s general admission. Visit cbmm.org/smallcraftfestival for more information.

Kent County Touch a Truck Ag Fest

Get ready for the Kent County Touch A Truck Ag Fest on October 7th from 10 a.m. to 3 p.m. at the Kent County Ag Center in Chestertown. There will be a wide variety of trucks and other vehicles on display to look and touch. There will also be plenty of activities for the whole family including scavenger hunts, pumpkin decoration, face painting, a petting zoo, and more. Find more information at kentcountyfair.org.

Easton Beer Fest

The 8th Annual Craft Beer Fest will be at The Easton Volunteer Fire Department on October 7th from noon to 4 p.m. This event is Maryland’s largest under cover craft beer festival with over forty breweries, wineries, and distilleries on site. The day will also include food, vendors, raffles, and more. Find more information and buy tickets at eastonbeerfest.com.

Rock the Reef 

The Chesapeake Bay Environmental Center’s 2nd Annual Rock the Reef will be held on October 28th from 5:30 to 8:30 p.m. at CBEC’s campus in Grasonville. The night will have live music by Red Betty & the Ruckus, food stations by Bark Barbeque Café and Harris Seafood, silent and live auctions, and more all to benefit CBEC’s Reef Restoration and education initiatives. Find more information at bayrestoration.org.

Fall Oyster Shuckdown

On Saturday, October 21st, Libbey’s Coastal Kitchen & Cocktails in Stevensville will host the 1st Annual Fall Oyster Shuckdown! Billed as a celebration of all-things bivalve, the event will feature heavy food stations starring oyster dishes, beer, wine, and live music with the Chesapeake Sons. Proceeds will directly benefit The Arc Central Chesapeake Region. For full details and to purchase tickets, visit libbeyscoastalkitchen.com/happenings.

Easton Airport Day

Easton Airport will host the 14th annual Easton Airport Day on Saturday, October 14th. The annual event offers a unique opportunity to visit the community airfield and learn about flying. Formation flyovers highlight the event with “Warbirds” flying patterns over the skies of Talbot County. Learn more at eastonairport.com.