Bite of Baltimore - Fells Point & Mt. Vernon Food Tour - All Year Long - Food. Facts. Fun. These are the 3 things we can promise on a Food Tour! Every Sat and Sun, Bite of Baltimore offers these amazing walking tours in the Fells Point, Mt. Vernon, or Federal Hill Neighborhoods. You will enjoy a progressive dinner (very filling!) consisting of 4 plates of food: appetizer, entrees, and desert along with a seasonal cocktail.

September:

Wine On The Beach - September 5-6, 2025 - Ocean City Inlet Park – Where the Boardwalk Begins. Featuring Wineries from Maryland, Micro-Brew beer and Domestic Beer for purchase, Delmarva Cuisine, Quality Arts & Crafts, Local Live Entertainment

Ocean City Seafood Festival – September 6, 2025 - Join us at Northside Park for a delectable waterfront experience featuring top Maryland restaurants, live music, and more!

Maryland Restaurant Week - September 12-21, 2025 - For ten days, we’re bringing all counties and all restaurants together to celebrate and support our industry. For the restaurants: There are no course requirements, no prix-fixe menus needed, and no entry fees. Participating restaurants may offer special menus, discounts, or seasonal fare for dine-in, curbside, or carryout. The dining public is invited to enjoy these Maryland Restaurant Week-specific specials.

Maryland Seafood Festival – September 13, 2025 - The Maryland Seafood Festival hosts loads of seafood vendors, local shopping and vendor options, a fantastic beverage selection with lots of local craft beer, live music, a crab soup cook-off and kids activities. Enjoy the day by the bay relaxing and this Maryland tradition of over 50 years!

Johnny Appleseed Festival - September 13-14, 2025 - The fall festival will celebrate our orchard heritage with apple pie and ice cream and anticipates a crowd of 5,000 over two days. Local businesses will share goods and services, and Paradise will host artisans from all over the state and beyond selling a variety of handicrafts.

Susquehanna Wine & Seafood Festival - September 20, 2025 - The festival will feature local restaurants and food trucks. Each restaurant will serve signature seafood dishes ranging from crab cakes, lobster rolls, grilled oysters, and fish tacos as well as Maryland steamed crabs (of course)! There will also be non-seafood fare available. In addition to delicious culinary offerings, the festival will feature wines, signature cocktails, and brews. The event will feature live music, cooking demos by local chefs, wine pairings, mixology demonstrations, unique shopping, a VIP tent and a family zone. Locals and visitors will get a chance to experience some of Maryland’s best seafood in a fun, casual, waterfront setting.

Trifecta Food Truck & Musical Festival - September 20, 2025 - Thirty-Five plus food trucks, Fifty plus vendors, Twelve plus awesome live bands, local craft beer & cocktails, free mechanical bull rides, axe throwing, the O's Bird and more.

The Big Dill World’s Largest Pickle Party - September 20-21, 2025 - Drawing more than 10,000 pickle fanatics, this annual festival features pickle-based cocktails and a pickle-based lager, pickle eating and brine chugging challenges,  music, comedy, food, and a fantastic kid zone with rock climbing, skee ball, and more. Join the party and see what the big “dill” is!

Calvert County Watermen's Festival and Boat Docking Competition - September 21, 2025 - Starting at noon at Watermen's Wharf at the end of Solomons Island. The Festival is perhaps best known for our Boat Docking Contest, during which work boats and charter boats compete within their divisions for cash, prizes and trophies.  Never a dull moment, this is a spectacular event to watch!  Beer, food and soft drink sales and exhibits by some of our sponsors will also be available. Live entertainment will be provided by Deanna Dove, the Island Girl herself. This year we'll also feature a Buoy Toss Contest for kids 7 and under, a Small Ahchor Toss (8-10 year olds) and a Large Anchor Toss for 11-14 year olds.
SEATING IS LIMITED SO PLAN TO ARRIVE EARLY!

J. Millard Tawes Crab & Clam Bake - September 24, 2025 - All-You-Can-Eat.Steamed Blue Crabs, Steamed Clams, Steamed Corn, Raw Clam Bar, Fried Clam Strips, Fried Fish, Sweet Potato Fries, French Fries, Onion Rings and Watermelon. Includes beverages with all-can-drink Iced Cold Pepsi and Bottled Water, Cold Draft Beer (with I.D.). Drink responsibly and bring a designated driver! Bring family, friends & co-workers to join us for a beautiful day by the Bay with musical entertainment and enjoy the finest seafood our local waters and watermen have to offer.

The Maryland Italian Festival - September 26-28, 2025 - Billed as the largest Italian festival in Maryland, this event has it all. Featuring live entertainment, carnival rides, beer, wine and cocktails, Italian food, cooking and wine demonstrations, a bocce tournament and more…this festival is a sure-fire recipe for a weekend of delicious family fun.

Taste of St. Mary's - September 27, 2025 - Spend your afternoon in the heart of Downtown Leonardtown sampling the best dishes that our local restaurants have to offer. This family fun event will have a wide variety of food and drinks, kid friendly activities, and a classic car show.

Taste of Cambridge - September 27, 2025 - In addition to the cook-off contest and local spirits tasting, the festival will include a Kid’s Zone, community performances, a vendor market, live music on the mainstage, and additional food and beverages for purchase.

Mount Airy Oktoberfest - September 27, 2025 - Something for everyone. Beer, food, music, kids entertainment and more. German style beer brewed locally by Liquidity Aleworks, Enjoy traditional German-style food from downtown restaurants, shop local in downtown shops, vendors, live music and more!

Fest of Fall Caribbean Wine, Food & Music Festival – September 27, 2025 - Fest Of Fall is a celebration of various aspects of the Caribbean culture, including cuisine, music, and art. The event features live performances of locally and internationally renowned artists. Attendees have the chance to sample wine and flavorful food, as well as admire jewelry, clothing, and craft supplied by multiple vendors.

October:

Taste of Bethesda - October 4, 2025 - The 33rd annual Taste of Bethesda is scheduled for Saturday and will feature Bethesda's best restaurants, five stages of live entertainment, an activity area for kids and more!

Darlington Apple Festival- October 4, 2025 - One day crafts festival in the small town of Darlington, in Harford County. Festival celebrates all things "apple," offering entertainment, art, country market, refreshments, and much more.

Quad State Beer Fest: Halloween Hysteria - October 4, 2025 - This annual event will see over 35 breweries plus wineries, cideries, distilleries and seltzeries! All alcohol samples are included in your admission in your festival tasting glass. Take part in numerous games and contests, browse & shop from dozens of vendors, and chow down on some scrumptious grub from the best local food vendors. Don't forget to dress the part in joining over 2,000 others in the Halloween festivities!

Crabs For A Cure Crab and Oyster Feast - October 7, 2025 - Benefits Bosum Buddies Charities, featuring steamed crabs, oysters, buffet, draft beer, and sodas. There will be a cash bar, and don't miss bidding on the silent auction items.

Maryland State BBQ Bash - October 10-11, 2025 - Great food, great music, great people, the Maryland State Barbecue Championship, and the MD State BBQ Bash Tailgate Challenge have combined to create a tradition that we hope you will want to be a part of this year and in the years ahead.

Westminster Oyster Stroll - October 11, 2025 - The Westminster Oyster Stroll Festival is far more than oysters, music, food, and fun for the community. It is an event designed to raise awareness about the importance of oyster aquaculture in the Chesapeake Bay.

Rock Hall Fallfest - October 11, 2025 - FallFest attracts thousands of visitors from across the eastern seaboard showcasing the quaint hamlet of Rock Hall as we celebrate our heritage as a waterman’s town. Locals and visitors alike attend the festival because they know that FallFest guarantees to be a unique event where musicians hold forth throughout the day, oysters are local and plentiful, and children can participate in captivating and free activities. Approximately 40 handicraft vendors show and sell their wares at the festival and a large selection of food vendors serve up regional favorites. We invite you to come and have a front row seat to our town’s legacy of working on the water.

Stella Maris Crab Feast - October 11, 2025 - Join us for an all-you-can-eat CRAB FEAST packed with delicious food, exciting games, raffles, and LIVE music! Come hungry, leave happy, and help make a difference. Let’s crack some claws for a cause! Your support helps us continue providing compassionate care to hospice patients and their families.

Savor Bowie Fallfest Food, Wine, and Music Festival - October 11-12, 2025 - Two Days of Complimentary Wine tastings from the areas best wineries! Vendors, Great food, Exhibitors and Artisans, Two stages and many areas of music and other entertainment, Showcasing the best of what the county and surrounding areas has to offer.

Good Beer Festival at Pemberton Park - October 17-18, 2025 - The Good Beer Festival in Salisbury, Maryland, offers unlimited tastings of craft brews, music, games, food and peddlers of crafty and unique items. Friday is the only nighttime beer festival on the Eastern Shore.

Oyster Festival at Captain Avery Museum - October 18, 2025 - Winner in the past of the prestigious Bay Weekly Best of the Bay award for Community Events -- features good community company, fine regional music, an array of choice gifts for purchase, a cash raffle, local food and drink and the best oysters anywhere. Come out for the festival and our biggest fundraiser of the year and enjoy the day on our broad green lawn on the banks of the West River in Shady Side.

Oktoberfest in Berlin - October 18, 2025 - Authentic Oktoberfest featuring 2 bands: The Edelweiss Band & The Dunehounds. Featuring brats, pretzels and Burley Oak beer, etc. Scales n Tales Show & the annual fall sidewalk sale. Free parking and shuttle from Berlin Intermediate School.

U.S. National Oyster Festival- October 18-19, 2025 - Traditional food festival focusing on oysters and the waterman's culture of Southern Maryland. Includes National Oyster Shucking Competition and National Oyster Cook-Off. Live music and entertainment, crafts, displays, Oyster and Craft Beer Tasting.

Pumpkins On The Green - Irvine Nature Center - October 24, 2025 - Known as the best fall party in the area featuring live music from the Jody West Band, spectacular food, refreshing drinks, and an extraordinary silent auction all under the big tent at Irvine.

Maryland Crabcake Festival - October 25, 2025 - Celebrate everything Crabcake and Maryland! Join 100.7 The Bay and WJZ-TV at the Carroll County Farm Museum in Westminster, Maryland. We are hosting some of Maryland’s finest Crabcake restaurants along with Food Trucks and Artisan Vendors! Beer and Wine. Live music from The Reagan Years, The Chesapeake Sons and Experience!! Celebrity Judges will select the winner of Maryland's Best Crabcake for 2025. Special Guests! All Ages-Kid-Friendly. Free Parking.

Chesapeake Bay Maritime Museum Oysterfest - October 25, 2025 - Features oysters served a variety of ways, along with other local fare, craft beer, and spirits, plus live music on two stages, an oyster stew competition, a full schedule of demonstrations and presentations, children’s activities, and more.