A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of October. Event dates may be subject to change.
U.S. Powerboat and Sailboat Shows
The U.S. Powerboat and Sailboat Shows are back this October. The Powerboat Show will be at Annapolis City Dock from October 6th through 9th. The Sailboat Show will take place one week later, October 13th through 17th. These shows are for all boat lovers to explore a variety of new and used boats as well as supplies, fishing gear, marine accessories, and much more. Find more information at annapolisboatshows.com.
Providence Center’s Harvest Bash
The original Harvest Bash is back. On October 15th, Providence Center is hosting their 8th Annual Harvest Bash at Providence Center’s Greenhouse and Gardens in Arnold. The bash will feature a feast of fall bounty, signature cocktails, raw oyster bar, custom donuts, live music, auctions, and so much more, all under twinkling lights and a canopy of stars in the greenhouse and gardens. This fundraising event raises critical funds to support over 300 people with intellectual and developmental disabilities to discover and live their best lives in Anne Arundel County. For more information, visit providencecenter.com.
What’s Up? Media’s Bridal Expo
Get everything checked off your wedding to-do list at What’s Up? Media’s one-stop shop on October 23rd at The Atreeum at Soaring Timbers in Annapolis. From cake tastings to beauty makeovers, we will have plenty of options for you to plan your perfect wedding. Plus, brides will receive a complimentary swag bag! Sample delicious desserts while visiting with wedding pros, get inspired at the fashion show, have fun in the photo booth, and enjoy live demos and exclusive wedding savings. Whether you are just starting your planning, finishing up last details, or anywhere in between, you will find exactly what you are looking for here! Find more information at whatsupmag.com.
International Edgar Allan Poe Festival and Awards
Experience mystery, intrigue, and the Macabre at the 5th Annual Poe Fest International on October 8th and 9th at the Edgar Allan Poe House & Museum in Baltimore. The free festival will be from 11 a.m. to 4 p.m. each day and feature Edgar Allan Poe themed performances, vendors, readings, music, and more. For more information, visit poefestinternational.com.
GiGi’s Playhouse Golf Outing
GiGi’s Playhouse Annapolis hosts their 3rd Annual Golf Outing at The Cannon Club in Lothian on October 17th starting at 9 a.m. This day on the golf course is to support individuals with Down syndrome, their families, and the community. In addition to a beautiful day of golf, the day will include breakfast, lunch, and post-game appetizers, beverages, a swag bag, and a longest drive and closest to the pin contests. Find more information at gigisplayhouse.org/Annapolis.
Annapolis Baygrass Music Festival
Get ready for a beach-front music festival with a mission to protect and restore the Chesapeake Bay. This weekend of music will feature 14 progressive bluegrass bands on two stages at Sandy Point State Park in Annapolis. This festival will feature locally sourced food, regional microbrews and wines, paddle boarding, yoga classes, local vendors, and kids’ activities. Baygrass blends the finest progressive bluegrass music with the perfect views of our Bay. The event will take place October 1st and 2nd. Find more details at baygrassfestival.com.
A Veteran’s Narrative
Through October 27th, the Gallery at MC3 continues to host A Veteran’s Narrative through Music and Art while partnering with Warrior Music Foundation. The project highlights six local artists and six local veterans that have been paired with each other to interpret the veteran’s story through artwork. MC3 has selected artists specializing in various mediums. MC3 will be hosting the reception for this exhibit on October 20th from 6 to 8 p.m. Find more information at mc3annapolis.org.
Art @ The Park
On October 15th and 16th, Quiet Waters Park is hosting the 32nd Annual Art @ the Park arts festival, featuring a variety of original visual arts along with demonstrations and live musical performances. All proceeds from the festival will go toward events and programs that are held in the park. For more information, contactfestival@fqwp.org.
Lifeline 100 Community Ride
On October 2nd, Anne Arundel Department of Recreation & Parks, Anne Arundel County Police, and Bicycle Advocates for Annapolis and Anne Arundel County (BikeAAA) are hosting the 8th Annual Lifeline 100 Community Bicycle Event. There will be a 100- and 65-mile scenic route option with views of the Severn River, Chesapeake Bay, historic Annapolis and more, or there will be paved trails for a flat 30- or 15-mile trail. Proceeds support local nonprofits including Anne Arundel Crisis Response System, Friends of Anne Arundel County Trails and Kinder Farm Park, and BikeAAA. All courses will start at Kinder Farm Park in Millersville. Register and find more information at lifeline100.com.
Friends of the Light House Bountiful Harvest
Saddle up for Friends of the Light House Bountiful Harvest: Boots & Bling! This fundraiser will be on October 15th from 6 to 10 p.m. at The Atreeum at Soaring Timbers in Annapolis. The event will include cuisine, an open bar, live and silent auctions, and live music by Misspent Youth. Show up in your country or cocktail attire to raise money for The Light House: a homeless prevention support center. Find more information at friendslhs.ejoinme.org.
Dragonfest Raffle & Party!
Annapolis Dragon Boat Club is kicking off Breast Cancer Awareness Month with a street party and raffle, after a morning of paddling for a purpose. The fundraiser party will be held at Pier 4 Marina in Annapolis on October 2nd. The day will be filled with live music, great food, local beer, amazing oysters, raffles, auctions, and so much more. Find more information at annapolisdragonboatclub.org.
Maryland Black Bears
The Maryland Black Bears are taking the ice for another season at the Piney Orchard Ice Arena in Odenton. The Bears have five home games this month. They play Danbury Jr. Hat Tricks on October 14th and 15th at 7:30 p.m., followed by the Johnstown Tomahawks on October 28th at 7 p.m., October 29th at 7:30 p.m., and on October 30th at 2 p.m. If you can’t make one of those games, the Bear’s season continues through mid-April! Find more information and buy tickets at marylandblackbears.com.
Casey Cares Golf Tournament
The Casey Cares Foundation will host its 19th Annual Golf Tournament on October 17th at 10 a.m. at the Cattail Creek Country Club in Glenwood. The outing includes a light lunch, raffles, prizes, and more. The evening will end with a cocktail reception. Companies are encouraged to register as foursomes and individuals are allowed. Not only will it be a fun day of friendly competition, but the event will also raise much-needed funding for the Casey Cares Foundation, which provides ongoing and uplifting programs for families with critically ill children. Find more information at caseycares.org.
Old Bowie Festival
On October 1st, from 11 a.m. to 5 p.m., enjoy the 2nd Annual Old Bowie Festival. Take part in a day of arts, crafts, music, food, children’s activities, and more fun on Chestnut Avenue and 9th Street in Bowie. Old Bowie has strong ties to the railroad and established itself as a growing, vibrant community. Since then, the city became home to people from an ever-growing collection of cultures. Find more information at oldbowiecelebrates.us.
Chesapeake Arts Center’s Arts in the Park Festival
Chesapeake Arts Center is having their 8th Annual Arts in the Park Festival on October 8th from 10 a.m. to 3 p.m. in front of the Hammonds Lane Theatre. The festival will include live performances, artists, and community vendors as well as multiple hands-on arts workshops, food trucks, door prizes, and fun for the whole family. Find more information and register for the festival at chesapeakearts.org.
Wanda Sykes Live!
Wanda Sykes is coming to Live! Casino and Hotel in Hanover. On October 7th at 9 p.m., the Emmy winning stand-up comic, writer, actress, and producer will take the stage. Sykes has been entertaining audiences all over the world for over 20 years, has ranked among Entertainment Weekly’s “25 Funniest People in America,” and won multiple awards for her comedy and performances. See her live at Live! this October. Order tickets and find more information at marland.livecasinohotel.com.
Easton Airport Day
The 13th annual Easton Airport Day is here! On October 8th, the Easton Airport will host the fun-filled gathering, which offers a unique opportunity to visit the community airfield and see what flying is all about. Formation flyers will highlight the event with “Warbirds” flying patterns over the skies of Talbot County. The event will feature rare and unique aircraft, military jets, and airport equipment as well as demonstrations, hands-on activities, and plenty of fun for the family. Find more information at eastonairport.com.
Academy Art Museum’s Annual Craft Show
The Academy Art Museum in Easton is hosting their 25th Annual Craft Show on October 22nd from 10 a.m. to 5 p.m. and October 23rd from 11 a.m. to 4 p.m. The show will feature more than 50 artists from across the country, with all proceeds supporting the Academy Art Museum and its mission to provide meaningful art experiences and education to the Mid-Shore. For more information, visit academycraftshow.com.
Queen Anne’s County Arts 45th Anniversary
Come together to celebrate the 45th Anniversary of Queen Anne’s County Arts on October 22nd at 6 p.m. at Kent Island Volunteer Fire Department in Chester. The event will include live music from Mike Hines and the Look, food, beer, wine, and plenty of entertainment. All sales will benefit the Queen Anne’s County Arts Council’s mission of promoting and supporting the arts in our community. Find more information at queenannescountyarts.com.
Rock the Reef Bash
The Wet & Wild Auction is back this year as the Rock the Reef Bash on October 29th. This annual fundraiser for the Chesapeake Bay Environmental Center’s Bay restoration efforts will have live music, silent and live auctions, raffles, food, and libations with a Halloween theme. The event will be 5 to 8:30 p.m. at the Chesapeake Bay Environmental Center in Grasonville. Find more information at bayrestoration.org.
Easton Beer Fest 2022
Support local by drinking local! The 7th Annual Craft Beer Fest will be held October 1st from noon to 4 p.m. at the Easton Volunteer Fire Department. This is Maryland’s largest under cover beer festival and features over 40 breweries, wineries, and distilleries. There will also be live music by Black Dog Alley. Get a VIP ticket for an extra hour of the festival. All proceeds benefit the Easton Fire Department. Get tickets and find more information at discovereaston.com.
Pump It Up for Hospice
Friends of Hospice and Talbot Hospice are joining forces for this year’s Winter Festival. To kick off this festival, Pump It Up for Hospice will take place on October 15th on Harrison Street in front of the Waterfowl Building in Easton. This unique community fundraiser will help raise money for The Talbot Hospice Foundation. The Winter Festival will continue in November with the Santa Fun Run 5K on 11/19, The Festival of Trees on 11/26, Carols by Candlelight on 11/26, and Talbot House Tours on 12/4. For more information, visit talbothospice.org.
