Saturday, September 20: The inaugural IRONMAN Maryland triathlon will be held in Cambridge. Join the fun as downtown Cambridge also celebrates with their annual Summer Send-Off event. The Summer Send-Off and its Blues, Brews, & BBQ is from 5-10 p.m. on the 300 and 400 blocks of Race Street. Visit the shops, dine out, and be a spectator as the athletes run by. For more information, please visit www.cambridgemainstreet.com.

Friday, September 26: The 24th Annual Chamber Challenge Golf Tournament will be held at the River Marsh Golf Course. The tournament includes18 holes of golf, use of cart, skeet shoot, and lunch. Proceeds will benefit education programs and other initiatives that support Dorchester County’s business community. To register or learn more, contact the Dorchester Chamber of Commerce at 410.228.3575 or by emailing info@dorchesterchamber.org.

Saturday, September 27: Come downtown and enjoy Crabtoberfest. The Oktoberfest-style event will take place from 4:00-10:00 p.m. on the corners of Race and Gay streets. American and German beer will be available as well as a plentiful variety of German and crab fare. Enjoy German folk dancing and carnival-style games. To learn more, contact the Dorchester Chamber of Commerce at 410.228.3575 or by emailing info@dorchesterchamber.org.

Sunday, September 28: The Eight Annual St. Michaels Concours d’Elegance will be held at the Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina. This year’s event will feature rare pre-war grand classics with European coachwork, wood-bodied cars, sports cars, classic wooden speedboats, and fashion. Tickets for general admission are $35, and VIP tickets are $100 and include lunch at the Hyatt Regency. Proceeds benefit the Mid-Shore Community Foundation. To find out more please visit www.smcde.org.