Six Reasons to Plan a Fall Adventure on Maryland’s Eastern Shore

Labor Day has come and gone, which means the unofficial end of summer. Before we know it, Pumpkin-flavored goodies will adorn grocery store shelves, the heat will begin to dissipate and the green leaves will give way to beautiful red and gold hues.

It’s never too early to plan your fall getaway to Kent County, Maryland. Autumn is a lovely time of year to visit the Eastern Shore, and with all of the fun local festivals and activities, it is a perfect time for a relaxing weekend at Great Oak Manor!

Check out these six reasons to visit Kent County, MD this fall:

  1. Gorgeous Foliage – With the arrival of fall come changing leaves and crisp breezes. Take the time to enjoy the magic of autumn: the blazing hues of crimson, amber, orange, and gold, before they wither into winter; a scenic drive down a winding, country road, or a few minutes to roll and play in the leaves with your inner child.
  2. Cooler Weather – Autumn brings with it much cooler weather so we can enjoy all the beauty of the outdoors without the heat and humidity. Enjoy a paddle in the Chesapeake Bay atop one of our standup paddle boards or kayaks, hit a few holes at the 9-hole executive golf course, or take a stroll along the shoreline. Whatever your choice, be sure to enjoy the beautiful weather before the cold and snow come!
  3. Oktoberfest – September 30, 2017 – Celebrate the fall harvest with amazing fall bounty prepared by Chef Kevin McKinney of K-B Market and Kitchen School, beer from Bull and Goat Brewery, wine from Clovelly Vineyards and Crow Vineyard & Winery, and music by the Free Range bluegrass band. Proceeds from the event support Colchester Farm CSA’s education programs. Tickets should be purchased in advance.
  4. Winery Tours – Move over Sonoma Valley! You don’t have to fly to California to experience vineyard hopping and delicious wine. The Eastern Shore has evolved into a wine hot spot! Spend your weekend strolling through the beautiful vineyards and sampling your new favorite wines on the Chesapeake Wine Trail.
  5. Ghost Tours – October 20-21 & 27-28, 2017 – Behold true tales of murder and mayhem; and folklore that still lingers from the region’s British and African heritage. Guides will take ticket holders aounrd the darkened streets of Chestertown by candlelight, sharing strange accounts collected from historic district home and business owners. For more information or tickets, click here.

    Tall Ship

  6. Sultana Downrigging – October 27-29, 2017 – The Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival is one of the largest Tall Ship gatherings on the East Coast. Visitors will see a waterfront filled with ships, schooners, and other wooden boats in one of America’s best preserved historic seaports. Other activities include: performances by world-class musicians; lectures by nationally recognized authors and filmmakers; opportunities to sail in part of a fleet of tall ships!
  7. BONUS: Great Oak Manor is pet friendly! No need to leave Spot or Rover at home. We have three pet-friendly rooms so your four-legged friend can enjoy all the fun fall events Kent County has to offer.

Great Oak Manor and the Eastern Shore are a great place for your autumn adventure. Be sure to book your room before all the leaves fall!