Annapolis Chocolate Binge Festival

West Street Annapolis, MD, United States

The  Annapolis Chocolate Binge Festival is now in it's fourth year. This family friendly festival includes entertainment, live music, chocolate, holiday shopping and the lighting of the festive West Street Holiday Light Canopy.  Take a walk along West Street and tour over 35 chocolate vendors selling all types of chocolate specialties, including chocolate truffles, caramels, and [...]

Yacht Party Macy’s Annapolis

Macy's 1295 Annapolis Mall, Annapolis, MD, United States

Come, You are Invited to experience something different in beauty. Specialty Services from Port to Port all around the World! Everything from Cairo Bronzed Goddess Glow to MemorizingFloral Scents from the pink sands of Greece. Your skin can get everything from a soothing facial to a hydrating moisture boost. Come have fun with us at [...]

Free

Corvettes on the Bay Fun Show Annapolis City Dock

Annapolis City Dock City Dock, Annapolis, MD, United States

Corvette Annapolis was founded in 1991 and is dedicated to the promotion of the Chevrolet Corvette, and camaraderie among Corvette owners in the greater Annapolis and Central Maryland area.  Come join us for a celebration of America’s Sports Car at our annual show. This Corvette-only Fun Show will occupy center stage at the historic Annapolis [...]

5th Annual Pints for Paws Homebrewing and Craft Beer Festival

Navy-Marine Corps Memorial Stadium 550 Taylor Ave,, Annapolis, MD, United States

The Annapolis Homebrew Club is a group of like minded individuals with various backgrounds, from various locations across Maryland.  While the club is primarily based in Annapolis, our members span across the entirety of Anne Arundel County and beyond. With a passion for brewing (and drinking), our members help promote the public awareness and appreciation [...]

$30

Truxtun Youth Triathlon

Truxtun Park 273 Hilltop Ln, Annapolis, MD, United States

Be challenged in a Swim, Bike, Run event at Truxtun Park! SWIM in the Truxtun Park pool; BIKE through City parks and adjoining roads; and RUN through Truxtun’s trails. All participants receive a medal for completing the race. Trophies are awarded to the 1st, 2nd, and 3rd places in each age group. Entry fee includes [...]

$55

Sunday in Annapolis, MD (Boating and Touring)

St. John's College 60 College Ave, Annapolis, MD, United States

Learn the history of the Naval Academy and Colonial Annapolis Lunch at one of Annapolis' most popular restaurants Enjoy a relaxing afternoon boat cruise on the Chesapeake Bay Spend a beautiful fun-filled day of activities in Annapolis, the capital of Maryland. 

$50

ENDLESS SUMMER 6-HOUR RUN

Greenbury Point Nature Center Greenbury Point Nature Center, Annapolis, MD 21402, Annapolis, MD, United States

Endless Summer 6 Hour Run is a low-key, special event hosted by the Annapolis Striders benefiting the Semper Fi Fund. Fast and flat scenic 3.5-mile loop, primarily on packed dirt paths around Greenbury Point across the Severn River from the U.S. Naval Academy. Solo and relay divisions. Course Fast and flat scenic 3.6-mile loop, primarily [...]

$45 – $75

2019 Maryland Seafood Festival

Sandy Point State Park 1100 East College Parkway, Annapolis, MD, United States

The 52nd annual Maryland Seafood Festival is a tasty and entertaining tradition, with music, great food, exhibits, arts and crafts, and featuring the 29th annual Crab Soup Cook-off. This family fun and feasting event draw 20,000+ visitors from all across the mid-Atlantic region. With live music performances, chef demonstrations, delicious seafood, creative craft booths, an interactive [...]

$10 – $120

Women’s Expo

Westfield Annapolis 2002 Annapolis Mall, Annapolis, MD, United States

Come out and enjoy a day that is unique for women’s! Grab your girls and join us at 2002 Annapolis Rd Mall between H& M and Metro Pcs at Annapolis, MD 21401 on Saturday and Sunday during the mall hours. Enjoy giveaways, shopping, food & fun. We will have a variety of local women in [...]

Free – $280

Twist & Stout

Quiet Waters Park 600 Quiet Waters Park Road, Annapolis, MD, United States

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, artisan vendors 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 [...]

$25 – $75
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