The Oaks Waterfront Hotel in Easton, Maryland is a boutique hotel that promises a postcard-worthy autumn escape. Expect luxury accommodations, seasonal dining, and cozy fall offerings, like fireside s’mores and warm spiced cocktails. Guests will also enjoy vibrant foliage reflected off the Chesapeake Bay and charming fall festivals. What’s great is your hotel is just a short distance from Baltimore, Philadelphia and Washington, D.C.
Here’s how a fall trip to The Oaks might unfold:
Day 1
- Afternoon Check-in: Arrive at The Oaks and settle into one of the hotel’s 11 elegant rooms or four private cottages with sweeping waterfront views—perfect for leaf peeping.
- Golden Hour Stroll: Explore the property’s 10 acres of landscaped grounds, enjoying the crisp fall air and fiery fall foliage.
- Dinner at The Oak Room: Grab a spiced fall cocktail at The Oak Room bar before heading to the dining room to enjoy autumnal dishes inspired by the Eastern Shore.
Day 2
- Explore Easton/St. Michaels: Take a complimentary chauffeured ride to the nearby towns of Easton or St. Michaels where boutique shops, fine dining and seasonal events like OysterFest (October 25) and the Waterfowl Festival (November 14-15) await.
- Pumpkin Patch Fun: Just minutes away, Family Affair Farms offers a classic fall outing with a u-pick pumpkin patch, corn maze and other autumn activities.
- Sail on the Chesapeake Bay: Enjoy a private evening aperitivo cruise aboard The Oaks’ Hinckley yacht and take in the colorful foliage reflecting off the Chesapeake Bay as the sun sets over the water.
- Relax by the Fire: Spend your evening cozied up around the outdoor firepit with a mug of hot cider and s’mores kit.
Day 3
- Brisk Morning Bike Ride: Hop on one of the hotel’s complimentary bicycles for a leisurely ride along quiet country lanes lined with golden maples and crimson oaks.
- Breakfast & Farewell: Savor your final morning at The Oaks with a gourmet, made-to-order breakfast crafted from fresh, seasonal ingredients.
