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Things to do in Middleburg

From classic must-see sights to insider hot spots and local haunts, there are countless things to do in Middleburg. How do you decide? Start with our travel guide and get our favorite Middleburg attractions and activities—shops, museums, parks, nightclubs, coffee shops, tours, and more.

Our international team of editors and writers handpick the best things to do in Middleburg to help travelers discover authentic, local experiences. Whether a hidden boutique with handcrafted products, a popular local festival, a bakery with a cult following, or a picnic-worthy park, Travel + Leisure guides the way, providing information and inspiration. From beaches and bars to cultural attractions and up-and-coming neighborhoods, our list will help you make the most of your romantic getaway, family vacation, or trip with friends. Below find Travel + Leisure’s top picks for what to do in Middleburg.

  • Chrysalis Vineyards

    Chrysalis Vineyards, located outside Washington, D.C. near Middleburg, Va., encompasses 71 acres on which 20 grape varieties are grown. Production ... More
  • Middleburg Spring Races

    A horseracing tradition for almost a century, this annual steeplechase event takes place during the third weekend in April at the Glenwood Park Rac... More
  • Middleburg Tack Exchange

    This 4,000-square-foot store sells horse riding supplies and specializes in English hunting tack and apparel. Clothing items for sale include frock... More
  • Virginia Fall Races

    Experience the horseracing traditions of Middleburg’s hunt country at the annual Virginia Fall Races, held the first Saturday and Sunday in October... More

Explore things to do in Washington D.C. Suburbs for more options.

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