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

Lights on the Bay

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

The whole family can enjoy the Lights on the Bay along the shore of the Chesapeake Bay, and this year marks the 20th anniversary of Lights on the Bay, held from November 21 through January 1. Weather permitting, the electric wonderland will be on full display nightly from 5:00 p.m. to 10:00 p.m. at Sandy Point [...]

Midnight Madness

Downtown Annapolis Annapolis, MD, United States

Select stores in downtown Annapolis will remain open until midnight to allow you to shop until the you drop! Also enjoy live music and holiday entertainment throughout the evening.

Fire and Ice

Annapolis Towne Centre 1906 Towne Centre Blvd., Annapolis, MD, United States

The Annapolis Towne Centre’s Fire & Ice Festival i on December 7, 2019, from 4-8 pm. Enjoy smores over a cozy fire, live music, a light show, on-site vendors, cocktails, shopping, and tasty bites.

MD State House by Candlelight

Maryland State House 100 State Circle, Annapolis, MD, United States

CYSO Senior Flute Ensemble will perform at the Maryland State House

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