Fall is officially here! Pick the perfect pumpkin, get lost in a corn maze, and enjoy other fall activities with the whole family at one of these Maryland farms. Learn More>>>
Annapolis and West County
Barkin' on the Bay – Watermark Cruises, Annapolis Thursday, September 26th, 6 p.m. Cruises on the Bay by Watermark presents a doggone good time to take your dog out on the water! Bring your dog for a cruise of Annapolis on Harbor Queen to benefit the SPCA of Anne Arundel County. Hot dogs can cool off in baby pools on the top deck. Guests will enjoy food from Graul’s Market, music, games, raffle items, and a cash and credit card well-stocked bar. Special treats will be served for our furry friends. Blazers. Bourbon. Cigars. – William Paca House and Garden, Annapolis Thursday, September 26th, 6 p.m. Join Historic Annapolis for its annual gentlemen-only evening. Network with fellow businessmen and community leaders while enjoying cigars, delicious food, and fine liquor tastings. All proceeds benefit Historic Annapolis. Taste of the Chesapeake – Crowne Plaza Annapolis Hotel, Annapolis Thursday, September 26th, 6 p.m. Join the Alliance for the Chesapeake Bay at our annual Taste of the Chesapeake for an evening of unique Chesapeake-inspired cuisine, local beer and wine, live music, raffles, and a silent auction! Rotten Tomatoes: MTPA Porch Stories – Maryland Theatre for the Performing Arts, Annapolis Thursday, September 26th, 6:30 p.m. TPA's Porch Stories is about bringing together members of the community to share, listen, laugh, and even cry at true-life stories. Every event is based on a new theme. September's theme is Rotten Tomatoes. We want to hear about your funniest/most horrific moment in the spotlight! Hoot & Hack Golf Tournament – Walden Golf Club, Crownsville Friday, September 27th, 8 a.m. Join the Herald Harbor Citizens Association for its second annual Hoot & Hack Golf Tournament. Registration includes breakfast and lunch, two beer tickets, and unlimited water, tea, lemonade, and coffee. ASO Opening Night Celebration – Maryland Hall for the Creative Arts, Annapolis Friday, September 27th and Saturday, September 28th, 6 p.m. The Opening Night Celebration is Annapolis Symphony’s favorite way to kick off the Masterworks Series. Get into the spirit before the concert by attending the Overture Party. Following the overture celebration, enjoy the first concert of the season! Hear Stewart Goodyear's Gershwin, Rachmaninov's captivating Symphony No. 3, and Beethoven's masterful Egmont Overture. The celebration continues after the concert! Meet Maestro Novo, Stewart Goodyear, and the wonderful Symphony musicians. Enjoy sweet treats, wines, and sparkling champagne. 30th Annual Kunta Kinte Heritage Festival – Annapolis City Dock Saturday, September 28th, 10 a.m. In September 1987, the Kunta Kinte Celebration, now known as the Kunta Kinte Heritage Festival, was born in Annapolis. The festival is a celebration of the perseverance, education, and cultural heritage of Africans, African Americans, and Caribbean people of African descent. Maryland Renaissance Festival – Crownsville Weekends through Sunday, October 20th Each autumn, the 27-acre village of Revel Grove in Crownsville comes to life with food, entertainment, and merriment during the Maryland Renaissance Festival. Enjoy nine weekends of jousting matches, juggling, handmade crafts, feasting, and more. Twist and Stout – Quiet Waters Park, Annapolis Saturday, September 28th, 12 p.m. Join Anne Arundel County Department of Recreation and Parks for its wine and beer festival, Twist and Stout. The festival will feature fine wine and craft beer from around Maryland, live music, gourmet food trucks, and artisan vendors. Proceeds will benefit the Quiet Waters Park Nature Center Campaign and the construction of new athletic fields in Brooklyn Park. Bands on the Bay: Oktoberfest – Camp Letts, Edgewater Sunday, September 29th, 1:30 p.m. Join the Celebrate Hope Foundation for a fun-filled day of live music, games, silent and live auctions, great food, and beer and wine. This year’s event will provide Dr. Anne Comi and her research team at Kennedy Krieger Institute with crucial funds for continued work on finding a cure for SWS and bettering the lives of those living with this rare disease. Oktoberfest – Annapolis Street, West Annapolis Sunday, September 29th, 12 p.m. The West Annapolis Business Affiliation presents the 29th annual Oktoberfest street festival! Enjoy great beer, great food, and great fun for the entire family. The event will feature several food vendors and beer trucks, as well as more than 130 artisans, crafters, and direct sales professionals.
Eastern Shore
Wine on the Beach – Ocean City Inlet Friday, September 27th and Saturday, September 28th Rediscover the best Maryland fare during Wine on the Beach. Now in its 25th year, this annual event has become an early fall tradition that celebrates the beauty of the Shore with the tastes and culinary delights of Maryland. Enjoy art and craft vendors, live entertainment, regional food, and a variety of offerings from local wineries and breweries. 5th Annual UWQAC Crab Feast – Harris Crab House, Annapolis Friday, September 27th, 6 p.m. Join United Way of Queen Anne’s County (UWQAC) for its annual Crab Feast at Harris Crab House. Enjoy all-you-can-eat crabs along with a buffet, draft beer, soda, and water. The event will also feature an auction, a 50/50 raffle, and music from DJ Jack Wilson. Mid-Atlantic Symphony Orchestra: Season Opener – Chesapeake College, Wye Mills Friday, September 27th, 7:30 p.m. Mid-Atlantic Symphony Orchestra (MSO) starts its 22nd season with its opening concert “From Movie Themes to Classics.” The concert will begin with Nicolas Mazmanian’s “Mission Impossible Variations” which was dedicated to Lalo Schifrin. After the Variations, Vincent Beer-Demander will join the orchestra for the American Premiere of Lalo Schifrin's Mandolin Concerto. The concert will conclude with Beethoven’s iconic Seventh Symphony. IRONMAN Maryland – Great Marsh Park, Cambridge Saturday, September 28th, 6:45 a.m. Cheer on triathletes as they swim, cycle, and run through scenic and historic Dorchester County during IRONMAN Maryland. The best place for spectators to enjoy the race is Great Marsh Park, where the race will begin, and at the finish line, located at Long Wharf Park. The is no admission fee to watch the race. The event will offer 40 qualifying spots for the 2020 Ironman World Championship in Kailua-Kona, Hawaii. Frederick Douglass Day – Easton Saturday, September 28th, 10 a.m. Join the Frederick Douglass Honor Society, the Town of Easton, and the Talbot County Free Library for a celebration of the life and legacy of Talbot County native Frederick Douglass. The celebration will be held in downtown Easton and features a variety of activities to educate and inspire the community and visitors about Douglass and how his writings continue to influence and share our future. 9th Annual Elf Classic Yacht Race – Chesapeake Bay Maritime Museum, St. Michaels Saturday, September 28th, 11 a.m. Guests are invited to CBMM to watch the ninth annual Elf Classic Yacht Race—held again this year on the Miles River. The race is sponsored by the Classic Yacht Restoration Guild and the Chesapeake Bay Maritime Museum, and is included with regular CBMM admission Mid-Shore Out of the Darkness Walk – Idlewild Park, Easton Saturday, September 28th, 11 a.m. Suicide prevention starts with everyday heroes like you. Join the American Foundation for Suicide Prevention as they walk to save lives and bring hope to those affected by suicide. Funds raised at the walk will benefit the American Foundation for Suicide Prevention. Be a part of a movement turning hope into action, and creating a culture that’s smart about mental health. 13th Annual St. Michaels Concours d'Elegance – Chesapeake Bay Maritime Museum, St. Michaels Sunday, September 29th, 10 a.m. Enjoy a day of grand classic motor cars, antique wooden boats, fashion, and style. Peruse rare, exquisite rolling works of art, including pre-war, coach-built, and award-winning sports cars. New this year, the Chesapeake Bay Maritime Museum will host the first annual Chesapeake Bay Motoring, held in conjunction with Concours d’ Elegance. Proceeds benefit the local chapter of the Antique Automobile Club of America. Osprey 5K and Fall Festival – Kent School, Chestertown Sunday, September 29th, 9 a.m. Held on the beautiful grounds of Kent School in Chestertown, the Osprey 5K is a family-friendly event for athletes of all levels of skill and experience. The race will consist of a 3.2-mile run. After the race, stick around for the Fall Festival. The event will feature fun activities for the whole family!
Regional
Das Best Oktoberfest – M&T Bank Stadium Saturday, September 28th, 6 p.m. Das Best Oktoberfest returns downtown at M&T Bank Stadium. This festival includes over 100 unique and diverse craft brews, wines, ciders, and schnapps from Maryland, Germany, and all over the world. Guests can also enjoy delicious German foods and other festival goodies, Oompah bands, live music, exciting contests, and much, much more! Sunday in the Country – Merriweather Post Pavilion Sunday, September 29th, 2 p.m. Enjoy a day of live music by hit country artists including Old Dominion, Michael Ray, Jordan Davis, Lauren Alaina, Dylan Scott, Jimmie Allen, Brandon Lay, and more!
