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 Town Center Fall Fest
From 11 a.m. to 2 p.m. on October 19th, celebrate all things Fall with Annapolis Town Center’s Fall Fest. This free fall fest will feature a pick your own pumpkin patch and decorating, DIY s’mores, face painting, a costume contest, photo ops, live music, and so much more for the whole family to enjoy. This event is free but be sure to bring canned food or a monetary donation to benefit the Anne Arundel County Food Bank. Find more information and reserve your spot at annapolistowncenter.com.
Photo by Larry French
Maryland Renaissance Festival
It is the final month for the 2024 Maryland Renaissance Festival in Crownsville. The final dates for this season’s Renaissance entertainment are October 5th, 6th, 12th, 13th, 19th, and 20th, from 10 a.m. to 7 p.m. each day. Be sure to get your last dose of jousting, merriment, turkey legs, and more this month. And in the spirit of harvest season there will be seasonal decorations and special performances. Get tickets today at rennfest.com.
Annapolis Powerboat Show
The Annapolis Powerboat Show will be a boater’s dream-come-true at Ego Alley and Annapolis Harbor on October 3rd through 6th. Floating docks will create a temporary marina to showcase new boats and premiering models, plus the latest boating accessories, equipment, and apparel right in our hometown. Bring the whole family to City Dock for a fun weekend celebrating powerboats. Find more information and get tickets at annapolisboatshows.com.
Annapolis Sailboat Show
Sailors from around the world will gather in downtown Annapolis for the Annapolis Sailboat Show on October 10th through 14th. This annual celebration lines the docks with sailboats, from multihulls to monohulls, cruisers, and racers, sailing dinghies, and more. Tents will have nautical gear, communication equipment, sails, and more for seasoned and novice sailors, and everyone in between. Find more information and get your tickets at annapolisboatshows.com.
Annapolis Symphony Orchestra Masterworks Season Opener
The Annapolis Symphony Orchestra’s 2024–2025 season, Music Matters, starts with three concerts this month under Artistic Director and Conductor José-Luis Novo. On October 4th and 5th at 7:30 p.m. Masterworks I: Pasajes will feature music from Tania León, Mozart, Bruckner, and Still with pianist Brian Ganz (pictured) at Maryland Hall in Annapolis. The same performance will take place on October 6th at 3 p.m. at the Music Center at Strathmore in Bethesda. ASO’s mission is to create connections with each other and throughout our community through music, so let’s make that happen this season! Find more information on Season 63 at annapolissymphony.org.
Bountiful Harvest – Costumes & Cocktails
The Light House is hosting the fundraiser, Bountiful Harvest – Costumes & Cocktails, on October 25th from 7 to 11 p.m. at The Atreeum at Soaring Timbers in Annapolis. The night will include live and silent auctions, live music by Noelle & Jeff Band, gourmet food by Light House Bistro, and an open bar, all to raise money for The Light House, a homeless prevention support center. Dress up in your favorite costume and raise some money! Find more information at friendslhs.org.
Photo credit Scenic Rivers Erin Valentine
2024 Lifeline 100: Scenic Rivers’ Ride for Land & Water
Choose between a 100-, 65-, 30-, or 15-mile bike ride winding through scenic Anne Arundel County at The Anne Arundel County Lifeline 100 Century Ride. The ride will start at 7 a.m. on October 6th at Kinder Farm Park in Millersville and will raise money for Scenic Rivers Land Trust. The rides’ scenic views will include the Severn River, College Creek, Spa Creek, South River, and the Chesapeake Bay. Be sure to register at srlt.org.
Chesapeake Arts Center’s 10th Annual Arts in the Park
The 10th Annual Community Festival at Chesapeake Arts Center, Arts in the Park, will be on October 5th from 10 a.m. to 3 p.m. The festival will bring together local residents, art enthusiasts, and community organizations for a day of vibrant entertainment, delicious food, interactive art activities, and more all on Chesapeake Arts Center’s campus in Brooklyn Park. Find more information about the free event at chesapeakearts.org.
Photo by David Trozzo Photography
Celebration of Philanthropy
For nearly 25 years, the Community Foundation of Anne Arundel County’s Celebration of Philanthropy Awards Luncheon has honored individuals, businesses, groups, and foundations who have demonstrated outstanding generosity and community leadership. This year, the event will be held on October 30th at Live! Casino Hotel in Hanover. This event plays a major role in amplifying philanthropy in Anne Arundel County by shining a spotlight on those who go above and beyond to support our community. Find more information at cfaac.org.
Hoedown on the Farm
Get ready to celebrate 28 years of the healing power of horses at the family-friendly Hoedown on the Farm benefiting Maryland Therapeutic Riding at their campus in Crownsville. Enjoy music, fun games, food, and a chance to win great raffle prizes. The boot-scootin’ good time will be on October 5th from 4 to 8:30 p.m. Find more information and get tickets at horsesthatheal.org.
Tacos & Tequila Fest
The award-winning Tacos & Tequila Music Festival is coming to Prince George’s Stadium in Bowie. This year the festival will feature the ‘I Love The 90’s Tour’ with a lineup you do not want to miss including Vanilla Ice, Treach of Naughty by Nature, Rob Base, All 4 One, and so many more. In addition to the music, there will be plenty of tequila to enjoy at the festival. Find more information and get tickets at tacosandtequilafestivals.com/bowie.
Swim & Paddle the South River
The 5-mile event of the summer, Swim & Paddle the South River, celebrates amazing outdoor recreation on the South River and supports the efforts of Live Water Foundation and Arundel Rivers Federation on October 6th in Riva. Novice and experienced swimmers and paddlers are coming together to support these organizations. This year, the party following the swim/paddle will embrace a luau theme with a small feast and celebration. Sign up for the fundraiser at arundelrivers.org.
250th Anniversary of the Burning of the Peggy Stewart
In October 1774, the people of Annapolis discovered that brigantine Peggy Stewart contained contraband tea that violated the colonists’ non-importation resolution. In response to public outrage, shipowner Anthony Stewart was forced to burn the ship. On October 19th, enjoy the largest living history event of the year by visiting Historic Annapolis properties—the Waterfront Warehouse, the Shiplap House, and Hogshead—to encounter local sailors, merchants, and business owners, and discover what they thought of this historic event. Hear live music, play colonial games, and much more. Find more information at annapolis.org.
Barktoberfest
On October 5th, find plenty of steins and canines while celebrating German-style beer, Bavarian food, and pawesome four-legged friends at Annapolis Town Center. This year is the second annual Barktoberfest where a portion of the proceeds go directly to the Anne Arundel County SPCA. The day will have traditional fun with the classic stein-holding contests, plenty of fall photo opportunities, yard games, and so much more. Find more information and register at annapolistowncenter.com.
Anne Arundel County Sheriff 5K Fall Festival
Visit the Anne Arundel County Fairgrounds in Crownsville on October 6th from 7 a.m. to 2 p.m. for the Anne Arundel County Sheriff 5K Fall Festival benefiting Chesapeake K9 Fund. Run in a beautiful setting alongside your dog to raise money for a great cause. Fun, fitness, and making a difference, what else could you do with your Sunday morning? Find more information and sign up at runsignup.com.
Sultana’s Harvest Party
Ready for an old-fashioned harvest fest? Sultana Education Foundation is hosting its Harvest Party at the Preserve on October 5th from 3 to 7 p.m. at Sultana’s Lawrence Wetlands Preserve in Chestertown. Spend a few hours surrounded by nature while you enjoy live bluegrass music with Flatland Drive, oysters on the half shell with the Kent County Waterman’s Association, a children’s petting zoo, pumpkin bocce, and so much more for the whole family to enjoy. Find more information at sultanaeducation.org.
OysterFest
The Chesapeake Bay Maritime Museum in St. Michaels invites you to celebrate the Bay’s favorite bivalve at OysterFest on Octoebr 26th. This annual festival offers an array of food and beverage options, highlighted, of course, by oysters served a variety of ways, plus fun for the whole family with live music, an oyster stew competition, an oyster slurp-off, oyster-themed demonstrations and presentations, retriever demonstrations, children’s activities, and more. Visit cbmm.org for information.
Rock Hall FallFest
Rock Hall, the quaint Eastern Shore watermen’s town, will host its 27th Annual FallFest on October 5th. The popular autumn celebration of community, live music, and the “return” of the mighty oyster. Main Street becomes a bustling pedestrian thoroughfare during the 10 a.m. to 4 p.m. event, with lots of food and drink, artisan vendors, two stages featuring continuous live music, and, of course, thousands of locally-harvested oysters on the half-shell. Rock Hall FallFest is nonprofit, with all proceeds going to community projects. For more information, visit rockhallfallfest.org.
Kent County Health Expo
The 2024 Community Health & Wellness Expo is just around the corner! On October 17th from 3 to 7 p.m., visit Kent County Family YMCA in Chestertown to celebrate healthy living for all in Kent County. The expo will include free health screenings, flu shots, free refreshments, entertainment, and over 60 exhibitors for all your health needs. Find more information about the event at homeports.org.
Rockin’ The Porch Party
One of the most anticipated fall events is back in Centreville on October 6th from 2 to 6 p.m. Queen Anne’s Centre for the Arts is hosting Rockin’ the Porch, a free community event in Downtown Centreville with live music, food vendors, and fun for all ages. Musical performances will take place on the porches of historic buildings with a wide array of genres including jazz, blues, party rock, country rock, contemporary, Latin, and orchestral sounds, with a rhythm and blues grand finale on the Courthouse Square. Find more information and a full list of performing artists at queenannescountyarts.com.
9th Annual Easton Beer Fest
The annual premier craft beer festival, which has sold out the last three years, will be celebrating nine years at Easton Volunteer Fire Department on October 12th from noon to 4 p.m. The festival will feature over 40 breweries, wineries, and distilleries pouring over 120 craft beers, ciders, seltzers, wine, and spirits from the Mid-Atlantic region and beyond. Get your tickets at eastonbeerfest.com.
Mid-Atlantic Small Craft Festival XLI
The Chesapeake Bay Maritime Museum in St. Michaels will host the Mid-Atlantic Small Craft Festival XLI on October 4th through 6th, welcoming one of the nation’s largest gatherings of small boat enthusiasts and unique watercraft back to its waterfront campus. A fall staple for four decades, MASCF invites guests to marvel at the craftsmanship and innovation used in traditional and contemporary small craft with dozens of examples showcased both on land and in the water. Festival entrance is included with CBMM’s general admission, which is free for CBMM members. Learn more at cbmm.org.
Patriotic Standard Flower Show
On October 5th from 1 to 4 p.m., visit Elks Lodge in Easton for the Patriotic Standard Flower Show. Think of a mini version of the world-famous Philadelphia Flower Show right here in Easton! Somerset County Garden Club and the eight other garden clubs of District 1 of the Federated Garden Clubs of Maryland Inc. are hosting the show. The show will include a Zinnia-Growing Challenge and judged exhibits by Accredited NGC Flower Show Judges. Find more information by reaching out to Ann Street at alstreet@comcast.net.
Chestertown Challenge Half Marathon & 5K Run/Walk
The Chestertown Challenge Half Marathon & 5K Run/Walk will benefit Kent Association of Riding Therapy on October 13th at Wilmer Park. KART provides therapeutic horseback riding and equine activities for the special needs community, and what better way to raise money than getting yourself active this weekend! Sign up for the race at townofchestertown.com.
Looking Ahead
A few events worth jotting down on your November calendar.
Sultana’s Downrigging Festival – November 1–3 in Downtown Chestertown; downrigging.org
Stars, Stripes and Chow Chili Cookoff – November 2 at Camden Yards, Baltimore; baltimorestation.org
Bull & Oyster Roast – November 2 at Bleues on the Water, Glen Burnie; partnersincaremd.org
CASAblanca Gala 2024 – November 2 at Westin Annapolis Hotel; aacasa.org
Waterfowl Festival – November 8–10 at the Waterfowl Festival grounds in Easton; waterfowlfestival.org
50th Annual Maryland Irish Festival – November 8 at Maryland State Fairgrounds in Timonium; irishfestival.com
18th Annual Fish for a Cure – November 9 in Annapolis; fishforacure.org
Beef, Bonfires & Cigars – November 9 at Prospect Bay Country Club in Grasonville; haven-ministries.org
Bay Bridge Run – November 10th on the Chesapeake Bay Bridge; bikesignup.com
