1. Rolph 's Warf Marina

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Chestertown, MD

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Rolph 's Warf Marina

3.3 (6 reviews)
Open • 8:00 am - 4:00 pm

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Chestertown Marina

Chestertown Marina

(7 reviews)

Well worth the trip up the beautiful Chester River, especially for one of the Chester's many…read moreregattas and for Chestertown's many annual festivals. Enjoy comfortable new Marina infrastructure and new restaurant (98Cannon) on site! Walkable to natural foods grocery store, liquor store, many restaurants, bars, coffee shops, bread bakery, Saturday Farmer's Market at Fountain Park, visitor's center, Realtors (visit me: Beth O at Coldwell Banker on Cross St!), gift shops, galleries, and apparel. Dogs are welcome! Wilmer Park is adjacent to the marina with a walking trail and a rails to trails bike/walking trail you can follow to Washington College where many musical, educational, and cultural events are held that are open to the public. The entire marina property was raised to handle higher water and sinking ground, the waterways were dredged to keep the tall ships coming for Downrigging weekend in Fall and Tea Party in Spring. The Schooner Sultana is a permanent resident here! The new marina facilities include: beautiful Ipe floating piers, brand new conditioned bathrooms, shower facilities, laundry, and a lovely marina office with a comfy lounge area and water view deck. There's a handicap accessible boat ramp, gas & diesel, pump-out, travel-lift, and transient slips available for all sizes. Of course there's also a friendly staff. Samantha and Chris are great to work with! Our boat (DOGONIT) is resident here & we love seeing all the new visitors that are coming in under sail and power from Annapolis and beyond. The new Marina does not have a mechanic on staff, but should you find yourself in need, you can call good local mechanics who will help you on site.

Bring your life vest with you when you get off your boat because the dock is sinking!…read more At high tide the water covered the dock in several places and was halfway up my calf when I was walking to shore. I also took a bad fall at low tide because the boards that submerge are so moss covered that it's like walking on ice. The boating amenities are ok, but coming back to the boat at high tide and finding our shore line hanging in the water because the dock was submerged was very disconcerting.

Safe Harbor Great Oak Landing - Harbor entrance

Safe Harbor Great Oak Landing

(7 reviews)

My husband and I are avid boaters and always looking for new places to spend the weekend within…read morereasonable proximity to Annapolis. This was our first stay at Mears Great Oak Marina and I give it a solid 3 stars. The property has every amenity you can think of and is great for families, pets, bar scene and people watching. The reason I deduct 2 stars is that the place is a little run down... which for $2.75 a foot along with the claim that it is a "premier resort" I expect more. For example, when approaching the docks, they are not well marked, and the high school dock hand is more interested in standing there looking cool and taking a selfie than directing you to your proper fairway and slip. The slips are poorly marked as well, and the docks have seen better days, although not the worst that I have seen. The marina "culture" is interesting as well, with lots of people hanging out at their very personalized slips (think grills, gazebos, and other paraphernalia). Along with lots of house boats and run down sailboats with liveaboards. Moving on to the restaurant, which channels "Kellermans" in Dirty Dancing, the prices and selection are very good. The place has been renovated, but still smells musty like the 1960s. There is also an old conference center attached to the restaurant that is awkward and needs renovating and I couldn't imagine actually using for any event. It's only redeeming value is the view. On the subject of renovations, I was cringing as I dialed the code on the bath house door thinking of "harvest gold" toilets from the 1960s, but pleasantly surprised. The owners must have spent all of their money on the bathhouses as they were beautiful with nicely updated large showers and vanities. Although I'm not sure if they are cleaned on a daily basis, but they were very nice. The pool and Jellyfish Joel's area were nice, fun, and entertaining, as well as the live music. I can't speak to the hotel but it looked old as well. All of the buildings on the property could have used a good power washing to remove the spiders and bug debris. In summary Fairlee Creek is a beautiful place to see and I am happy that we stayed for the weekend. However if Mears Great Oak Marina wants to be the "premier" resort that it claims to be, it needs to take a few tips from Herrington Harbor.

https://www.fairlees.com/menu Very good cheesesteak. Freshly…read morechopped (chunky style, which I love) ribeye, Cooper sharp and very thinly sliced onions. Only negative, not nearly enough onions. If they can pick up their onion game, this would be a really good cheesesteak, especially for this area. But, as it stands, excellent flavor. I'll be back for sure.

Rolph 's Warf Marina - marinas - Updated October 2026

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