1. Sailwinds Park

    1. Sailwinds Park

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    Cambridge, MD

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    View from boardwalk.
    Leo Y.

    A great place to stretch one's legs after a long drive. Right off route 50, with restrooms, information, playground, ample parking, and about a mile of boardwalk. Plenty of people fishing, kids playing on the playground, a few bikers and joggers on the boardwalk. If the boardwalk is followed under route 50, there is an impressive pedestrian bridge parallel to route 50.

    Caroline N.

    It was worth the pit stop =) I was driving on the bridge, on 50E towards Ocean City. My butt was hurting from driving about 2 hours, and I just randomly spotted a "park/grassy-lookin' area" from the bridge... and literally just took a turn off the highway and decided to just check it out and see if it was a nice view of the water... Although I only briefly walked around for 10 minutes, playing some phone games and whatnot - the view was WONDERFUL. Wow, you get to be literally right against the beautiful water AND bridge! I can tell this would be a great place to take the kids, as there are a couple playgrounds. As a grown adult, I passed on the playgrounds - BUT I LOVED sitting on the SWINGING BENCHES. There's multiple of them! =) What a nice touch!!! I didn't check out the bathroom/building facility, but it looked big from the outside. Pretty sure this place is kept up with maintenance - it was pretty clean in general, with no trash laying around. I think I'd come again if my legs start hurting from long drives to the ocean!

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    Review Highlights - Sailwinds Park

    There was also a shaded area to have a picnic, family swings and a nice view on the water and a bridge.

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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!

    Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina - Health Club

    Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina

    (302 reviews)

    $$$

    This is such a fun spot! I came here for a weekend conference and was able to take advantage of the…read moreamenities, but they had made to choose from. I enjoyed the pool, walking around the golf course and nature areas, fire, pits, and the feeling being secluded while also being across the street from a Walmart and some other retail. The indoor pool was family friendly, and had a hot tub you could be indoors or outdoors in, which was fun. They also had a hot tub outside closer to the water, but it was a little chilly so I didn't go out there. There were a ton of pools outside that looked nice even though I didn't take advantage of them The conference spaces made the work side of my trip easy since they have a variety of different meeting rooms and a larger spaces. Their channel is pretty good with two peloton and other machines and weightlifting areas. The meal options were pretty good for a hotel, the salmon over couscous that we had for dinner one night was really good. Coming to the eastern shore over the winter is always so peaceful and the Hyatt made it easy for me to enjoy it. The staff were friendly and helpful even when I messed up my booking, they were able to fix it right away.

    This was our second time staying at the Hyatt Regency Chesapeake Bay and, unfortunately, our…read moreexperience was very mixed. The positives first: our Petite Suite was spacious and comfortable, the recreational facilities kept our family entertained, and the premium parking option was absolutely worth it for the convenience. Unfortunately, the food and beverage experience fell far short of expectations. While the fly problem was slightly improved compared to our previous visit, flies were still everywhere throughout the property. At the breakfast buffet, there were dead gnats on the fruit, which raised serious concerns about food safety. Dinner in the main restaurant was disappointing- the food quality was poor, 2 separate meals contained a hair, missing food items were never followed up on, and the servers often seemed unfamiliar with the menu or service procedures. The takeout window was consistently slow, and the main bar appeared dirty during our visit. This is a beautiful resort with great amenities and plenty of potential, but the dining operation needs significant attention. Better food safety practices, improved staff training, cleaner food and beverage areas, and more attentive service would make a tremendous difference. Until those issues are addressed, it's difficult to recommend the resort based on the overall experience.

    Layton's Chance Vineyard & Winery - Bridal shower

    Layton's Chance Vineyard & Winery

    (41 reviews)

    $$

    On a beautiful sunny Saturday in October we stopped at Layton's Chance to sit back and enjoy some…read morewine. We each had a flight of six (Vintner's flight and Lazy Day flight) both delivering a couple of good options, but we enjoyed the Lazy Day flight more. The grounds are cute. We found some adirondack chairs to sit back and relax. There's a decent amount of outdoor seating but as it gets more crowded it's a good idea to bring your own chair as recommended on their website. There were no events on this day, but Layton's Chance does hold many events throughout the year that appear to be very popular. I noticed some of their upcoming holiday functions are already sold out. After finishing our flights it was on to the much raved about wine slushies. You can get small (12oz) or large (16 oz). It is with good reason the slushies are mentioned a lot in the reviews. Oh my they are delicious!!! The featured flavors on our visit were peach bellini and one made with the Freedom wine. Of course we capped off the visit with some bottles to take home and the mix to make the slushies.

    We did a wine tour to learn the history of Laytons winery. Also included a free tasting. They have…read moresweet, semi sweet and dry wines available. Nice giftshop area with seating available. We purchased three bottles of wine. Including their 100% watermelon. So refreshing for the summertime. Very nice place to visit and chill with some wine.

    Sailwinds Park - venues - Updated July 2026

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