October means sweaters, pumpkins, and, in Maryland’s case, great concerts. Rather than over-indulging in Halloween candy, treat yourself to some live music. For a more extensive list of musicians and bands coming to the area, visit our online calendar at Whatsupmag.com. Don’t forget to check out the October music preview playlist at the bottom of the page. Here are a few of the concerts headed our way in the coming weeks:
Phil Collins
Melissa Etheridge
Florence + The Machine
Eric Hutchinson & The Believers
Jonny Lang
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Taste of the Chesapeake – Crowne Plaza Annapolis Hotel
Thursday, September 27th, 6–9 p.m.
Join the Alliance for the Chesapeake Bay for Taste of the Chesapeake. Enjoy and evening of delicious Chesapeake-inspires culinary creations, local wine and beer, live music, and silent auction items at the Crowne Plaza Annapolis Hotel This event raises critical funds to support Chesapeake Bay restoration.
Blazers. Bourbon. Cigars. – William Paca House and Garden
Thursday, September 27th, 6–9 p.m.
Join Historic Annapolis at the William Paca House and Garden for the original premiere Gentlemen's only evening. Enjoy bourbon, whiskey, and scotch tastings along with cigars, delightful food, and an array of vendors.
Paws About Town – Union Jack’s
Friday, September 28th, 5:30–7:30 p.m.
A social series bringing dog friendly restaurants, pet loving charities and community canines together! Join us on a local restaurant tour, enjoying different people & pup menus while supporting a different local animal charity each month. This month, proceeds will benefit Ben’s Memorial Fund.
Kunta Kinte Heritage Festival – Susan Campbell Park
Saturday, September 29th, 10 a.m.–7 p.m.
Enjoy the rich heritage of Kunta Kinte whose story from the Gambia to Annapolis and for generations on down was told in the book Roots: Saga of an American Family by Alex Haley. A family-friendly cultural festival celebrating the history and Heritage of people of African American, African, and Caribbean descent. This is the 29th year of this celebration that includes a full day of live music, dance, ethnic foods and wares for sale.
Twist and Stout – Quiet Waters Park
Saturday, September 29th, 11 a.m.–5 p.m.
Anne Arundel County Department of Recreation and Parks will present Twist & Stout, a fine wine and craft beer festival that also features live music from some of the region’s best bands, food trucks from around the state, and artists creating on site. Set at the picturesque Quiet Waters Park in Annapolis, MD, the activities provide the perfect ambiance for a fun-filled Fall day in the park.
Playlist Pub Crawl – West Street
Saturday, September 29th, 12–5 p.m.
The inaugural Playlist Pub Crawl will take place on West Street to benefit Music 4 Vets. Participating locations currently include Metropolitan Kitchen & Lounge, Stan and Joe's, Ram's Head Tavern, Fado Irish Pub. benefit Music 4 Vets, a program of Music 4 More. Music 4 Vets provides instruments and resources to music therapy programs that work with Veterans and active military across the United States.
28th Annual Oktoberfest – Annapolis Street
Sunday, September 30th, 12–6 p.m.
Join West Annapolis Business Affiliation as they celebrate their 28th Annual Oktoberfest street party. There will be plenty of beer, food, shopping, and even a polka band. This is a family friendly event.
Eastern Shore
Pull! for The Arc Clay Shoot Classic – The Point at Pintail, Queenstown
Friday, September 27th, 8:30 a.m.–2 p.m.
Come Pull! for The Arc on Maryland's Eastern Shore. Enjoy local foods, craft beverages, and friendly competition for a great cause. All proceeds benefit The Arc Central Chesapeake Region, proudly serving people with intellectual and developmental disabilities in Anne Arundel, Caroline, Dorchester, Kent, Talbot and Queen Anne's counties.
Wine on the Beach – Ocean City
Friday, September 28th through Saturday, September 29th, 11 a.m.–7 p.m.
Rediscover the best of Maryland fare during Wine on the Beach. Now in its 24th 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. Knowledgeable vintners will help educate visitors on characteristics of each selection. Beer aficionados have a choice of craft breweries to choose from, with a few hard ciders available as well.
Ironman Maryland Triathlon – Cambridge
Saturday, September 29th, 8 a.m.
The IRONMAN Maryland Triathlon is hosted by Cambridge and Dorchester County. The race offers a fast bike course and flat run through a quaint rural part of the Eastern seaboard, including Blackwater National Wildlife Reserve, ending in historic downtown Cambridge. Spectators can enjoy watching from Great Marsh Park, as well as Hambrooks, Water, High, and Poplar Streets along the run course. The race ends at Long Wharf.
Waterman's Triathlon – Town of Rock Hall
Saturday, September 29th and Sunday, September 30th
The Waterman’s Triathlon returns to beautiful Rock Hall. The swim takes place in Rock Hall Harbor on the Chesapeake Bay, protecting athletes from any serious wind or chop. The bike course is a triathlete’s dream with beautiful ribbons of pavement and wide shoulders throughout most of the rural course. The run course is pancake flat and takes athletes through the quaint nautically themed neighborhoods and side roads of Rock Hall
Out of the Darkness Walk – Idlewild Park, Easton
Saturday, September 29th, 11 a.m.
Suicide prevention starts with everyday heroes like you. Join the American Foundation for Suicide Prevention for a 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.
Family Day @ CBMM – Chesapeake Bay Maritime Museum
Saturday, September 29th, 1–4 p.m.
Get hands-on with our campus! Your family will have a chance to explore CBMM through hands-on activities and family-friendly exhibits, perfect for a day of family fun. Take a Quest Card and find your way around campus, trying your hand at caulking in the Shipyard like Frederick Douglass, walk on a giant map of the Chesapeake Bay, and climb to the top of the Hooper Strait Lighthouse.
Casino Night – Oxford Community Center
Saturday, September 29th, 6 p.m.
Join Oxford Community Center for its first ever Casino Royale, a twist on the OCC’s traditional cabaret event. Play games like Blackjack, Texas Hold ‘Em, and Roulette for a chance to win amazing prizes.
Western Shore
Trawler Fest – Baltimore’s Inner Harbor
Thursday, September 27th through Saturday, September 29th
Enjoy the nation's best in-water display of cruising powerboats, latest marine products and services, first class boating seminars and demonstrations, and rendezvous style evening events at the 2018 Trawler Fest Boat Show.
Baltimore Book Festival – Baltimore’s Inner Harbor
Friday, September 28th through Sunday, September 30th, 11 a.m.–7 p.m.
The 23rd annual Baltimore Book Festival returns to Baltimore’s Inner Harbor. The festival includes appearances by hundreds of local, regional, and national authors, book signings, more than 100 exhibitors and booksellers, poetry and book readings on multiple stages, live music, children’s activities, and plenty of delicious local food.
Baltimore Brunch Festival – Baltimore’s Inner Harbor
Saturday, September 29th, 6–10 p.m.
Head to Harbor Point in Baltimore for the Baltimore Brunch Festival. Enjoy food samples, mimosas, and Bloody Marys from some of the city’s best brunch spots at this all-you-care-to-taste brunch extravaganza.
WPOC Sunday in the Country – Merriweather Post Pavilion, Columbia
Sunday, September 30th, 2 p.m.
Enjoy a day of live music by hit country artists including Brett Eldredge, Dan + Shay, Dustin Lynch, Devin Dawson, Morgan Evans, Jimmie Allen, and Jillian Jaqueline.
