Easton, Maryland
Easton, Maryland

The Perfect Fall Getaway in St. Michaels

Discover a charming autumn getaway that combines stunning natural beauty, local culture, and a touch of history. Make The Oaks Waterfront Hotel your home on Maryland’s Eastern Shore to explore the idyllic St. Michaels area during its most picturesque time of year. As the leaves change and the air turns crisp, this region becomes a haven for fall enthusiasts. From boat cruises on the Chesapeake Bay to savoring seasonal delights at the St. Michaels Farmers Market, there’s something for everyone. Here’s a curated list of activities that will make your fall escape unforgettable!

Fall leaves in Maryland

Narrated Boat Cruise: A Scenic Fall Foliage Journey

Kick off your fall getaway with a memorable Narrated Boat Tour from Patriot Cruises around the Chesapeake Bay. As you glide across the serene waters, you’ll be treated to a breathtaking display of fall foliage. The vibrant hues of red, orange, and gold paint a stunning picture against the backdrop of the bay. Keep your camera ready to capture the local wildlife that often makes an appearance during this season. It’s a relaxing and picturesque way to immerse yourself in the beauty of autumn and pick up some interesting historical tidbits.

fruit at a local fall market in Maryland

St. Michaels Farmers Market: A Feast for the Senses

For a taste of the region’s finest offerings, make a stop at the St. Michaels Farmers Market. Here, you’ll discover a cornucopia of fresh, locally grown produce, delectable baked goods, and artisanal products. The market’s vibrant atmosphere and friendly vendors make it a delightful experience for the whole family. Whether you’re looking for a farm-fresh apple pie or a jar of homemade jam, you’ll find it here, making it the perfect place to stock up on autumn treats.

Car show

Cars & Coffee Classic Motor Museum Saturdays: Fuel Your Passion

If you’re a car enthusiast, the Cars and Coffee Classic Motor Museum Saturdays are can’t-miss events. Imagine sipping a cup of coffee while surrounded by a stunning collection of classic cars. It’s a sensory delight for those who appreciate automotive history and design. You’ll have the opportunity to chat with fellow enthusiasts and soak in the nostalgia of these beautifully preserved automobiles.

oyster festival in Maryland

Oyster Festival: A Celebration of Chesapeake Bay’s Bounty

OysterFest, hosted by the Chesapeake Bay Maritime Museum, is a vibrant celebration of the Chesapeake Bay’s rich maritime heritage and its famous oyster culture. This festival brings together seafood enthusiasts and history buffs for a day of delectable oyster tastings, live music, boat rides, and educational programs. Set against the stunning backdrop of St. Michaels, Maryland, OysterFest offers a unique opportunity to savor the flavors of the bay while appreciating its maritime traditions, making it a cherished annual event for locals and visitors alike.

Mid-Atlantic Small Craft Festival: Appreciate the Art of Boating

The Mid-Atlantic Small Craft Festival gives visitors the opportunity to see a beautiful collection of small boats and traditional watercraft, witness on-water demonstrations, and immerse yourself in the rich maritime heritage of the region. It’s a day of nautical adventure you won’t want to miss!

Couple looking with binoculars on a fall getaway in Maryland

Fall Birding and Waterfowl Festival: A Feathered Paradise

For birdwatchers and nature enthusiasts, St. Michaels offers a unique opportunity to witness fall migrations and spot a variety of bird species. Get outside together and spot beautiful species or check out the annual Waterfowl Festival, featuring art, exhibits, and birding tours that allow you to appreciate the area’s rich birdlife. Keep an eye out for waterfowl like ducks and geese as they make their seasonal stopover in the Chesapeake Bay.

Couple toasting glasses

Lyon Rum Distillery: Savor the Spirit of Fall

If you’re in the mood to warm up as the temperatures drop, head over to the Lyon Rum Distillery. Take a tour of the distillery to learn about the fascinating process of crafting award-winning rums. Of course, no visit is complete without sampling some of their finest spirits. It’s the perfect way to get into the “spirit” of fall and enjoy a unique local experience.

Sunset over the Chesapeake Bay in Maryland

1879 Hooper Strait Lighthouse: A Glimpse into History

Step back in time and visit the 1879 Hooper Strait Lighthouse at the Chesapeake Maritime Museum. Explore the lighthouse’s historic quarters and gain insights into the life of a lighthouse keeper. The panoramic views from the top are especially enchanting in the fall, offering a spectacular vista of the surrounding autumn landscape.

Couple eating a romantic dinner

Enjoy the Local Cuisine: Culinary Delights Await

To cap off your fall escape, be sure to explore the culinary scene in St. Michaels and nearby Easton. Both towns boast a variety of fabulous restaurants that offer fall-inspired menus. A special highlight is Bistro St. Michael, where you can savor delectable seasonal dishes that showcase the best of local ingredients. From hearty soups to savory entrees, you’ll find plenty of options to satisfy your autumn cravings.

Guest Room at The Oaks

Relax at Our Fall Haven

Nestled on a secluded cove on the Eastern Shore, The Oaks Waterfront Hotel is your ultimate destination for a magical fall getaway. Here, the beauty of autumn unfolds before your eyes with a backdrop of fiery foliage reflecting in the bay’s tranquil waters. The hotel’s amenities, from a cozy fireside lounge to plush guest rooms, are tailor-made for a snug autumn retreat. Imagine sipping on local coffee or a glass of fine wine as you relax in your luxurious room, suite or private cottage, or while you gaze at the water views from our manicured grounds. Your fall adventure starts here, so seize the opportunity and book your stay with us to immerse yourself in the enchantment of St. Michaels in autumn – it’s a season you’ll cherish for a lifetime.

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Water inlet at waterfront wedding venue and hotel in Maryland