Upper Chesapeake trip: Kent Narrows, MD to Potomac River - destinations to visit along the way

Also thinking about wandering up the Chester River for a weekend trip, looks like Rock Hall is on the river? Is that a good place to spend the weekend or are there other options?

Any other destinations North of Kent Island we should check out?

We also love the Chester River. Many great creeks to explore however we keep going back to the Conquest Beach. It’s a great spot for day trippers but we have stayed overnight there many times. There will be 20+ boats there on a nice weekend. There is a nice sandy bottom and good views. It is open to some wind but usually the Chester River is protected.

We have also anchored in the Corsica River just off the Chester several times.

Rock Hall is good for site seeing, lunch or dinner. On the North West side of Rockhall is Swann Creek, a great anchorage spot if you have a dingy. If you don’t have a dingy there a couple nice marinas. You can walk or ride bikes from there over to Rock Hall.
 
Looks like we could do Chestertown and Tolchester over a 2-3 day trip. Where do you recommend staying in Chestertown where we can get around on foot? Chestertown Marina looks nice, close to town. No online reviews though.

@Pirate Lady how come I have a feeling you have a favorite Tiki bar everywhere?
 
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Looks like we could do Chestertown and Tolchester over a 2-3 day trip. Where do you recommend staying in Chestertown where we can get around on foot?

@Pirate Lady how come I have a feeling you have a favorite Tiki bar everywhere?

They are in opposite directions from Kent Island. You'd do better to do them in two trips. Rock Hall/Tolchester in one, Chestertown the other.

Chestertown is immensely walkable. There's really only one marina - run by the city of Chestertown. It has a decent restaurant (98Cannon) and it's basically at the bottom of Main Street. You just walk to town. It's only a couple blocks further from the marina than St Michael's/Higgins was.

For Rock Hall, if you want to walk to town Rock Hall Marina is probably best. It's in the central Rock Hall basin, right between Harbor Shack and the Waterman's Inn. Visit both. It's about 1/2 mile walk to town. Osprey Pt and Haven Harbor (on Swan Creek, "behind" Rock Hall) are much nicer marinas. Both have free bikes you can borrow to scoot into town.
 
They are in opposite directions from Kent Island. You'd do better to do them in two trips. Rock Hall/Tolchester in one, Chestertown the other. .
Yeah, the more I looked at the maps you are correct.

Thanks for the feedback.
 
While your near Tolchester just around the corner so to speak, is Frairlee creek. There is also a marina there Great Oak, part of the Safe Harbor chain. In season there is a beach bar with bands and a pretty cool beach setup. Also a great place to hang on the anchor overnight. One of our favorite spots.

As mentioned up the Chester is Conquest beach, it's alright not much there unless you have a dinghy. It's on the way up to Chestertown, also on the way is another beach bar, the Sandbar. The Chester river in general is a very nice spot to anchor out and explore a bit.

Annapolis is ok, staying at "Ego Alley" can be interesting at times, but the best place to walk around town from. We'll get a mooring ball and dinghy in for that. There are nice town mooring spots all around Annapolis and they also have launch service. The thing with Ego Alley is you are stern in to the walk way and everyone walks by and stares at your boat, while your hanging out on it. really no privacy at all. But if you have not been to Annapolis, then it is a must see stop. Lot's of history there.

If you are going to stay at Rock Hall, stay at Haven Harbor South, great view of the harbor and a nice marina in general with a sort of beach bar that's nice. But walking distance to Watermen's another great hangout with good food as well.
 
... If you want a marina and still be near downtown you can try the Yacht Basin. ...

Yep, we stay at the Yacht Basin and walk to Lewnes' steak house and Chart House, great restaurants, but there in East Port right next to Annapolis. Much better and more relaxing, quick walk over to Pussers as well.
 
The Chester River looks narrow the more you travel north. Can I run at cruise all the way to the Port of Chestertown Marina? Navionics is saying I can, but...
 
Yeah, I am not feeling the Annapolis love here so that is why I am looking at north destinations now.

No Annapolis love? It's where the US Naval Academy is. The tour is spectacular given the rich history of the Academy. The town has great sites and great eats. They usually have free shows on the back side of the Academy near the water during the week. I spent two or three days there and felt like I didn't see it all. On Wednesday nights they have sailboat races every week. I personally love the area.
 
Downtown Baltimore is another fun trip. Lots of places you can Uber to. Great restaurants, good comedy clubs, etc.

Fairless Creek at Great Oak Landing is a fun marina.

Rockhall is a good time.

Going up the Sassafras river is fun. Sandy bottom river. Brackish water.
 
No love on where to stay, a marina. We are not ready to moor/anchor out yet.

As mentioned, stay at the Yacht Basin. Great marina.

The Chester River looks narrow the more you travel north. Can I run at cruise all the way to the Port of Chestertown Marina? Navionics is saying I can, but...

Yes you have lots of room on the Chester all the way to Chestertown no problem anywhere on that run. Just watch the buoys. I have run full cruise all the way in deep water, well deep for the Chesapeake.



As for the remarks about staying in Baltimore. I will be nice and say save that for another time after you do some research. Very nice place during the day for the most part but very dangerous at night away from the boat. Especially if you don't know where to stay away from.
 
As for the remarks about staying in Baltimore. I will be nice and say save that for another time after you do some research. Very nice place during the day for the most part but very dangerous at night away from the boat. Especially if you don't know where to stay away from.

I have to laugh! Funny not funny!
 
The Chester River looks narrow the more you travel north. Can I run at cruise all the way to the Port of Chestertown Marina? Navionics is saying I can, but...

NO!

Let me explain. The river is plenty wide, and even when it narrows near Chestertown there is a plenty-wide channel to stay in without any issue. BUT... there is a no wake zone (pretty well marked) at Rolph's Wharf Marina, about 3/4 the way up the river. They are militant about the no wake zone and will call you out on the VHF (by name) and tell you to slow down. I've heard rumors they've actually sent chase boats after violators. The marina is right on the river, so very exposed to someone blasting through with a big wake, so their concern for wakes is well founded. But it's probably best to drop down as you pass. There are usually No Wake markers there.

Also, the Chester River Yacht club is on the port side just prior to Chestertown. I've never seen No Wake markers there, but you should respect the No Wake as you pass in front of them, too, so you don't blast them. The channel takes you towards their side of the river.

These are short no wake zones and do not take away from the trip up the Chester. It's a beautiful ride. And it's even better in the autumn. Don't miss out on it.
 
I have to laugh! Funny not funny!

Laugh because it's true or you think it's safe in Baltimore at night?

If the later, just watch the news every morning and watch the death toll rise. Not safe at night in Baltimore if your not from there, and why take the chance?
 
I have to laugh! Funny not funny!

Also, true not true. I live in the City and my boat is here. That means I can walk to my boat any time I want. Can't beat that! Yes, there are some bad places in the City, but they are not along the waterfront. Yes, it's a city so things can happen. But that's true of just about anywhere people gather. There are plenty of places in the counties I wouldn't go either. In reality, it's not the battleground that so many people (without knowledge) claim it to be. If you want some recommendations on where to/not to dock in the City, I'll be happy to provide them. But message me directly as I don't want to get into a debate about how awful the place is with people whose information is gleaned from the TV.
 
... Also, the Chester River Yacht club is on the port side just prior to Chestertown. I've never seen No Wake markers there, but you should respect the No Wake as you pass in front of them, too, so you don't blast them. The channel takes you towards their side of the river.

These are short no wake zones and do not take away from the trip up the Chester. It's a beautiful ride. And it's even better in the autumn. Don't miss out on it.

Yep. no wake through there as well.

The Rolph's Wharf is home of the Sandbar beach bar. Nice stop if your looking for something to do, not a destination.

http://www.rolphswharf.com/?fbclid=IwAR26VpLqhHbLtKEJE-K-bq4Dd42HCBQ-NqpjPDi6jiE3mzC7Lmy8pzXAac4
 
Also, true not true. I live in the City and my boat is here. That means I can walk to my boat any time I want. Can't beat that! Yes, there are some bad places in the City, but they are not along the waterfront. Yes, it's a city so things can happen. But that's true of just about anywhere people gather. There are plenty of places in the counties I wouldn't go either. In reality, it's not the battleground that so many people (without knowledge) claim it to be. If you want some recommendations on where to/not to dock in the City, I'll be happy to provide them. But message me directly as I don't want to get into a debate about how awful the place is with people whose information is gleaned from the TV.

Look I knew when I posted this I would get backlash. Not saying the city as a whole is bad, and you can pretty much go anywhere you like during the day, at night is a very different story the later it get's news or not. I know first hand been going to Baltimore for work for many years and in all the wrong area's.

My saying dangerous at night is for anyone that doesn't know where to stay away from. Of course you know where to go and where not too, but others not from Baltimore will not know. The area around the Rusty Scupper is fine at night, go across by the Tiki bar and not so much.
 
Look I knew when I posted this I would get backlash. Not saying the city as a whole is bad, and you can pretty much go anywhere you like during the day, at night is a very different story the later it get's news or not. I know first hand been going to Baltimore for work for many years and in all the wrong area's.

My saying dangerous at night is for anyone that doesn't know where to stay away from. Of course you know where to go and where not too, but others not from Baltimore will not know. The area around the Rusty Scupper is fine at night, go across by the Tiki bar and not so much.

Actually, we wrote at the same time. I posted my comments before reading yours. I wasn’t directing my comments at you.
 

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