1. The Willow Grande

    1. The Willow Grande

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    Claiborne, MD

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    Osprey Point Retreat and Conference Center - Dining/conference on lower level, rooms above - all with spectacular views.

    Osprey Point Retreat and Conference Center

    (2 reviews)

    Located 90 minutes from Baltimore and Washington, Osprey Point is a serene and spiritual place that…read morefeels like the large home in which I'd like to live someday. Both secular and religious organizations host conferences here. Amenities include a large meeting room, free WiFi, office services for printing and faxing, tennis courts, a swimming pool and jacuzzi, a library, a chapel, workout facilities, recreation room with pool table and fireplace, a top chef (Dawn McLoughlin), and, of course, spectacular views of the Chesapeake. It is the perfect location for your next gathering (from 10 to 50 people). Golf, bay cruises, kayaking, and the charming town of St. Michaels are all within 20 minutes of the property. The property is operated by the Trinity Forum (www.ttf.org), a D.C.-based Christian 'think-tank' whose mission is to renew Christian culture and to promote human freedom and flourishing. The property is home to the Trinity Forum Academy (academy.ttf.org), an organization that annually enrolls approximately a dozen 20-somethings for a post-graduate year of study on an aspect of Christianity of interest to them. The fellows are housed in a separate building on the property.

    I spent the weekend at Osprey Point Retreat and Conference Center to conduct a site visit for my…read moreclient groups. I wasn't sure what to expect since it appeared to be in the middle of an extremely small town but not the usual B&B that you find in these rural Eastern Shore areas. Gorgeous tree lined and winding roads on the way in, bayside homes with tons of land, horse farms; everything you'd imagine a postcard to look like. We encountered about 20 deer bounding in front of us and luckily we were only going 3mph and able to stop. It was unlike anything we've ever seen. The land is protected and wildlife such as rabbits, geese and white tail run freely to the waters edge and back into the woods. Upon arrival, we toured the rooms and grounds. The property itself has one conference room and flexible small group event spaces designed to facilitate group discussion and reflection. Each of the 25 sleeping rooms has its own distinct design, simple and indicative of the region. Some rooms have porches and many face the water. It's awesome just to sit and listen to the water. There are no televisions in the rooms, so come prepared to RELAX and UNPLUG! The living and game room were comfortable and relaxing and do feature a television as does the small gym. The GM is gracious and hospitable and lives on the grounds and easily accessible. I will say for the city slickers and those unfamiliar with the area, do not expect a high end, boutique B&B catering to couples and others looking strictly for a getaway for the weekend. This functional venue and its space is designed and ideal for small social, civic, church and gov't groups. The grounds are shared with the Trinity Academy, a group of students completing a 9 month spiritual fellowship. The students make up most of the staff. It's great for off site retreats and brainstorming sessions with teams and leaders. Seems great for family events such as small and intimate vow renewal and weddings who want the feel of a B&B but need something a bit larger (keep in mind, there are 25 sleeping rooms). The city is small but within close proximity to St. Michaels and Easton. After my weekend, I decided to really start focusing on what's important and trying my best to SLOW down and appreciate the smaller things. It really does only take a couple days away from it all to see the difference a change of pace really makes. My husband commented the time seemed much slower, the days longer. Don't we all want need that sometimes!

    Chesapeake Paradise

    Chesapeake Paradise

    (8 reviews)

    A perfect experience, especially if you are a crabber. House is very well equipped for any kind of…read morecooking. Location is 5 miles from the grocery store, Chris Fine Foods. It's quiet. The view is both the creek and the bay. Lots of comfy outdoor furniture. They provide all you need to crab right off the dock. We caught at least 80 from there in 3 days. They provide a cleaning station and out door cooker for steaming crabs. Kayak a canoe and life jackets are provided as well. Kayak down the creek if you have little experience. Others can head out to the bay and down the coast. Host respodes to questions quickly. We will be back

    My family absolutely loved our stay at Chesapeake Paradise. The house is magnificent and had…read moreeverything you can imagine. We enjoyed the view over the creek extending out to the bay, and the many areas to have fun in the sun (the kids absolutely loved the room to run around outside and take a break from their tablets), or to hide in the shade of the screened in porch where we still enjoyed the view. There was fun to be had by everyone from 5-68 years old. My husband enjoyed crabbing (he caught lots of crabs and they were delicious) while others enjoyed the canoes and kayaks. I enjoyed relaxing looking out at the water during the day and spending time on the balcony off the main suite watching the moon and stars over the water. Quiet and relaxing atmosphere. There was something for everyone to enjoy. Shawn and her team were friendly and responsive to all our requests before, during and after check-out. I look forward to returning next year, if not before. This may have become my new home away from home.

    Chesapeake Bay Maritime Museum - Beautifully restored lighthouse

    Chesapeake Bay Maritime Museum

    (61 reviews)

    When I started planning my very first trip to St. Michaels, there was one attraction that made the…read moreitinerary before almost anything else: the Chesapeake Bay Maritime Museum. I'd heard so many people rave about it that I figured it deserved a few hours of my vacation. Turns out...a few hours wasn't nearly enough! Admission was $22 for adults, and one of my favorite surprises was learning that your ticket is good for two consecutive days. A volunteer at the front desk gave me a wonderful overview of the property, explained how everything worked and made sure I knew I was welcome to come back the following day as long as I didn't lose my admission sticker. That's tremendous value for everything there is to see! The first thing I realized after walking through the doors? This isn't just a museum. It's an entire waterfront campus! The Chesapeake Bay Maritime Museum sits right on the Miles River and includes historic buildings, floating vessels, exhibitions, gardens, a working shipyard where traditional wooden boats are still restored and built, and enough history to keep you wandering for hours. Whether you're interested in Chesapeake Bay history, boats, lighthouses, watermen or simply beautiful places to explore, there's something here for just about everyone. Now...in true to me fashion...I headed straight for the gift shop before I looked at anything else. My philosophy is simple: shop first, think about it while I explore, and if I still love it by the time I leave, I already own it. Except...that didn't exactly happen this time. I found something I loved immediately, bought it right away and happily carried my purchase around the museum for the rest of my visit. RELATED SIDEQUEST & PRO TIP: While I was wandering through the gift shop, I overheard another visitor asking an employee if they sold U.S. Lighthouse Society Lighthouse Passport books. Wait...what passport?! Excuse me while I casually eavesdrop. A very quick Google search later, I had fallen headfirst into yet another travel rabbit hole. Apparently there's an entire Lighthouse Passport Program where visitors collect official lighthouse stamps from locations all over the country. Well...that sounds dangerously like something I would absolutely obsess over! The museum has an official lighthouse stamp available at the front desk, so even though I don't own the passport yet, I stamped a blank piece of paper to tuck safely away until I order one. I have a sneaking suspicion I'll be back to stamp the real thing someday! PRO TIP: Get your lighthouse passport before you go! I spent the next several hours wandering the campus completely at my own pace. One thing I really appreciated was that the museum lets you create your own experience. Some exhibits fascinated me, others I breezed through, and there was never any pressure to see things in a particular order. It felt more like exploring than touring. The museum itself was fantastic and easily worth the $22 admission. More than anything, I came away impressed by how much pride everyone there takes in preserving and sharing the history of the Chesapeake Bay. It's clear this isn't simply a collection of artifacts. It's a place that's actively keeping an important part of Maryland's history alive. Whether you're visiting St. Michaels for a weekend or just passing , I'd absolutely recommend making time for the Chesapeake Bay Maritime Museum. And while you're there...don't forget to get your lighthouse passport stamp!

    The museum has a variety of experiences showingcasing the history and stories of the Eastern Shore…read more The models were in pristine condition. I look forward to returning for one of museums boat tours. Their new exhibition, Stories from the Shoreline was an excellent introduction to the culture of the Chesapeake region. My daughter loved the interactive exhibits at the museum.

    Tidewater Inn

    Tidewater Inn

    (126 reviews)

    $$$

    This is our first time in Easton, MD. Tidewater Inn is at the heart of the city. Perfect location…read moreto stay and explore Easton. We came right before Christmas. It's clean, the staff are welcoming. Rooms are clean. Just a couple of things - the glass on top of the bed side table had really pointed corners, my little toddler ran into couple of times and I did also. Definitely Not very safe for children. Bathroom sliding door had us laughing. You can see and hear it all.. you really gotta love the person staying with you cause it's gonna get next level intimate lol.. Convenient and cute.. not sure if I'll stay here again though.

    What a fabulous surprise! I was in the area and wanted to grab breakfast. I checked the menu and…read moresaw something that had been a mystery for many years. Scrapple. I have never ventured to try it and I have always assumed that it was undigestible and disgusting. But I decided that if it's on the menu at this swaggy establishment that I may as well give it a try. I went for the eggs with scrape. I never expected it to come out so fancy. It was cooked to perfection and the eggs were the perfect cook for such an adventure to my tastebuds. It had a fresh bed of greens that we're drizzled with a vinegarette. Everything was delicious and the staff was amazing. I actually dropped my wallet and couldn't find it for one day and when I called they said it was in the manager's office. Kudos to an amazing staff and establishment. I found out upon retreaving my wallet that they have a great HH and that on the first Friday, it's a special hh so I will be back!

    The Willow Grande - venues - Updated September 2026

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