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.

August:

Howard County Restaurant & Craft Beverage Weeks - August 11-24, 2025 - A delicious celebration of food, flavor, and local pride. Whether you're a seasoned foodie or a curious explorer, this is your chance to taste your way across one of Maryland’s most exciting and inventive dining destinations. Howard County’s culinary scene is a tapestry of global inspiration, seasonal ingredients, and unexpected twists. From tucked-away gems to well-loved favorites, you’ll find restaurants that bring creativity, culture, and community to every plate.

Maryland Vegan Eats Summer Fest - August 23-24 2025 - Vegan Restaurant Month is BACK AND BETTER THAN EVER! Along with their month-long celebration of plant-based eating, they are bringing the premier event of the month, "Maryland Vegan Eats Summer Fest", to POWER PLANT LIVE!!!! Our two-day national festival brings people from around the world to introduce veganism and to educate, inspire, and empower health-conscious and health-curious individuals to become better versions of themselves. Enjoy mouth watering grub while listening to music for the soul. Dive into great cooking demos and surround yourself with folks with good energy.

National Hard Crab Derby - August 29-31, 2025 - Come on down to Somers Cove Marina for a toe-tappin', crab-crackin' good time at the National Hard Crab Derby Concert Series! Get ready to groove to live music by talented local artists while enjoying a happy time with old friends. This in-person event promises a lively atmosphere and plenty of delicious crab dishes to savor and special drinks quench your thirst. Don't miss out on this exciting opportunity to celebrate Maryland's favorite crustacean in style!

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.

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.