My husband and I are going to Tilghman Island for a long Labor Day Weekend. We are staying at the Black Walnut Creek Inn. We are planning on doing a lot of relaxing on hammocks, renting kyaks, reading, etc. but would suggestions on:

Where to eat - specific suggestions for each meal. I think we get breakfast at our B&B - although we are not opposed to going out. Lunch - anything is fine. Dinner - we'd like some upscale suggestions. Will surely be heading into St. Michaels so suggestions there and other nearby towns would be great.

What to do - anything we shouldn't miss? All ideas are welcome!

Thank you!

The Inn at Phillips Mill just outside St. Michaels has a gorgeous view and is quite upscale for dinner - they also have a little less pricey pub for a meal. 208 Talbot on the main drag in St. Michaels is also good and pretty upscale.
I love blue crabs so we always have one meal at the Crab Claw restaurant at the marina. The maritime museum is right there also and is a nice diversion.

Sorry, I meant the Inn at Perry's Cabin, which is in St. Michaels. The Inn at Phillips Mill is in New Hope, PA. - also good, but not the one I meant!!

And there I was, musing about what the odds were of finding two different inns with such an unusual name. LOL

I was just in St. Michael's last weekend (sailed there) to celebrate my anniversary. We had dinner at 208 Talbot, and it was fantastic. On Saturday nights, they do a prix fixe menu at $55/person; they offer regular menu items (which you can see on their website) as well as specials. Service was outstanding, as was the food.

In the past, we've also gone to Town Dock restaurant. The food is excellent, but the place overall has an overcrowded touristy vibe.

For each place, reservations are key. St. M. gets quite crowded on summer weekends, and I imagine a holiday weekend would be even worse.

on tilghman:
- the bay hundred restaurant on the knapps narrows--right before you head over the bridge to tilghman--is good. mid-summer they opened a new outdoor seating area/bar with picnic tables under shady trees. food is decent and casual and it is fun to watch the boat traffic.

-across the narrows, the bridge restaurant is a touch more upscale. service is a bit patchy.

-i've never eaten at tilghman island inn but they are supposed to be good.

-harrison's isn't that great, imo

adding to the above listed in st. michaels (agree you should have reservations for dinner, labor day weekend will be crowded):
- the bistro is excellent

- 208 talbot has a happy hour from 5p-6p with 1/2 price wine and small plates. makes for a nice start to the evening.

- another favorite start of mine is having a drink from the perry cabin pub and enjoying it on the lawn. i haven't found the food in the main restaurant at perry cabin to live up to its reputation (and cost). i do enjoy the lighter fare in the pub.

- if the weather is nice, the deck at the shore lounge in the harbour inn has the best views of the harbor. and it is covered with an awning. they have a limited menu though.

- unless you are just getting crabs, i wouldn't recommend the crab claw.

further afield in easton, you can't go wrong with:
- inn at easton for the best meal in the area. amazing!
- out of the fire
- general tanukis
- mason's (good sandwiches for lunch too)

there are also a couple good restaurants in oxford but that is getting quite far from tilghman island.

have fun!

Wanted to say that I agree with everything that the previous poster said-- literally everything.

Also: Don't miss taking a leisurely stroll of the historic part of St Michael's, the back lanes and streets, etc. They're quite charming, with lovely small gardens and some fine old house (unpretentious). You can get a walking tour guide from the visitor's center. You can also rent a bicycle if you enoy that. And I believe there's a boat tour of some sort-- goes up the Miles River a bit. IMO worth doing if you've never been on those waters.
Another way to get on the water a bit is to take the Oxford-Bellevue ferry: gets you onto the handsome Tred Avon River (another branch of the Choptank). And I think Oxford is a town worth strolling also. (famous old yachting center)
Enjoy!

Thanks for the great suggestions! I will definitely make a reservation at 208 Talbot and do some of the other ideas.

One more question: How big is St. Michaels - in terms of how much of a day could you spend exploring/shopping there?

I have eaten at 208 Talbot a few times. We met friends there for lunch last weeken..very, very disappointing...so go for dinner.
Julia's in Centreville is getting great reviews.
For me St. Michael's onits own is an afternoon...and only then if you like to shop.

st. michaels is small. its main drag of shops is no more than a 1/2 mile long. how much time you need to enjoy it depends on how much you like the shops, enjoy strolling past historic homes, or just sitting by the water watching the harbor boat traffic.

most people find the maritime museum very interesting and it could take some time to go through depending on how much you enjoy that sort of thing.

you should try to get out on the water. take a skipjack cruise out of dogwood harbor on tilghman or at the very least go on the patriot out of st. michaels (poss mentioned it above). it travels up the miles river and provides a narrative on the area and the historic estates you pass. it leaves from the path that leads down to the museum and crab claw.