The Chesapeake Experience

Explore the shore: When the weather cools down, The Eastern Shore heats up with many great events to complement your family getaway or weekend adults-only escape! 6 OCTOBER: Get into the Halloween spirit with hayrides, pumpkin decorating, and other fall traditions. 6 Crabtoberfest at Sailwinds Park 13 Harvest Festival at Layton’s Chance Vineyard 28 The Kite Festival at Sailwinds Parks NOVEMBER: Plan your visit around our annual Oyster Days, with an Oyster Cookout and beer tasting yours for the sampling! A variety of family activities, live music, local art, and the popular Oyster Cup round out the celebration. Looking to take a break from the kitchen this Thanksgiving? Let us prepare your holiday feast while you relax with your loved ones. 9-11 Waterfowl Festival 21-25 Oyster Days Hyatt Regency Chesapeake Bay 24 Cambridge Christmas Tree Lighting DECEMBER: Make it a weekend for the kids to meet the big guy at our Breakfast with Santa! Stay for indoor swimming, arcade games, and more. 1 Cambridge-Dorchester Christmas Parade and Crab Tree Lighting 8 Santa Swim 31 New Year’s Eve at the Hyatt Regency Chesapeake Bay Resort NEW YEAR’S EVE AT THE HYATT REGENCY CHESAPEAKE BAY GOLF RESORT, SPA & MARINA. Ring in the New Year with something for everyone, enjoy a variety of complimentary activities including bounce houses, game rooms, balloon drop, live music, and more. Celebrate at one of our many restaurants or rejuvenate with champagne and a spa treatment. We look forward to celebrating with you. Starting at $ 239 plus taxes and resort fees. Additional terms and conditions apply. Photo by Jill Jasuta