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Great Outdoor Activities in and Around Annapolis MD

Appleton Properties | June 27, 2017

The capital city of Maryland has plenty to offer when it comes to outdoor activities and events. Here are some of our favorites.

  1. Annapolis Arts and Wine Festival

    One of the key city events, the Annapolis Arts and Wine Festival is a weekend affair that showcases the best art in the city. Aside from art for sale, live art demonstrations, and food trucks, the Annapolis Arts and Wine Festival also features 20 of the finest wineries in Maryland.

  2. Breakfast on a Boat

    Known as the sailing capital of the United States, it comes as no surprise there is such a thing in Annapolis as having breakfast on a boat. Charter one of these special 75-foot sailing yachts from Annapolis and it’ll take you and your loved ones on a relaxing cruise.

    The cruise is actually an overnight activity. It starts with a two-hour sunset sail, after which everyone aboard will disembark for a beautifully-prepared dinner in a top Eastport restaurant. After dinner, all guests will return to the yacht. Morning will eventually come, and with it, your delightful breakfast on a boat.

  3. Eastport A Rockin

    Held at the Annapolis Maritime Museum, Eastport A Rockin is an annual summer music festival that features a wide range of musicians, from rock and roll stars to jazzy ensembles. Eastport A Rockin is divided into three stages to accommodate a large audience. Local artisans also come and join the fun to present and sell their wares. As for the kids, they can spend the rest of their day in the children’s area, which is filled with a ton of fun activities such as laser tag, face painting, and moon bounce.

  4. Go wind- or kite-surfing

    Chesapeake Bay is one of the best places in the Mid-Atlantic to go wind- or kite-surfing. Just bring your gear, and even your kayaks and canoes on a good windy day. Some of the parks along Chesapeake Bay make for great launch points for these water activities. When you’re done, stash your board somewhere safe and grab some food at any of the restaurants along waterfront Annapolis.

  5. Annapolis Arts Week

    This year, Annapolis celebrated its first Art Week, which ran from June 3 to 11 in the city and in Anne Arundel County. Annapolis Arts Week includes a bevy of activities, including street parties, live music entertainment, art exhibits and more.

    Aside from the Annapolis Arts and Wine Festival (which we mentioned earlier), the Annapolis Arts Week also includes the following festivals: the Annapolis Irish Festival, the First Sunday Arts Festival, and Paint Annapolis.

    Annapolis Arts Week is a great way to see the city and feel its cultural vibe, as the week-long festivities will take you on a tour of some of the city’s most exciting parts and lauded art galleries.

There’s more of Annapolis to discover. Explore the Annapolis area, including the eastern and western shores of Chesapeake Bay. You can read more about that adventure here. For more information about Annapolis real estate, contact Appleton Properties today at 301-652-2707 or 202-888-4846.

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