OK, I’m not too familiar with Cooperstown area other than Ommegang (beer) and the Fly Creek Cider Mill which is a cute small place which has different kinds of cider and is a couple miles? north of the center of town. And I’ve never been to Table On Ten. I know the Mid Hudson Valley better, so here’s some thoughts:
On your way back from Cooperstown to Woodstock, I’ve only heard good things about Peekamoose Restaurant, it’s about 25 minutes west of Phoenicia. Bear Cafe is also supposed to be good (in Woodstock); we’ve been to New World Home Cooking in Woodstock several times if you’re looking for something a little more casual.
I’m not big on breakfast places, but Sweet Sue’s (Phoenicia) is known for their pancakes; I ate there a few years ago when we were in the area.
If you want to go to Saugerties, there are a few smaller places. Side trips that are not food are Opus 40 and the lighthouse at Saugerties on the Hudson, walk through 1/2 mile of brush to get there (which also doubles as a B&B at night).
Kingston is near there, and I’ve always been a big fan of Elephant Tapas Bar. It’s not all tapas, and is a combination of local ingredients + other influences (sometimes Spanish, sometimes other). The music can get loud later (80s/90s alternative and punk) so that might be a turnoff, but the food is delicious. Wine is mainly Spanish. I’d compare it in some ways to Central Provisions in Portland.
Rhinebeck - farmer’s market on Sundays. It’s smaller than some of the Maine markets, but it’s probably the best around here. Kingston has one on Saturdays as well. Favorite place to eat is The Local. Haven’t eaten at the Amsterdam yet, but I know the chef (from previous places) is good. If you’re looking for Napolitano style pizza, check out Pizzeria Posto. Cinammon Indian is very good - all places right near center of town.
Another place with Spanish influenced dishes is about 15 minutes north of Red Hook, in Tivoli, Panzur. Cute little town that just appears out of nowhere.
For Hudson - a great place to walk around if you want to see the architecture from 100+ years ago, and a city that had down days and is coming back to life. A few antique stores on Warren Street and a sense of hipsters (sorry!) but you’ve also got a New England square in the center of town. My favorite place is a pricey tasting menu (Crimson Sparrow), but their menu centers around seafood with Asian flavors, so that might not be up your alley. Other a la care dishes are all good, however. Backbar has a former NYC chef as its owner and is southeastern flavorful Asian dishes with great cocktails. His main place is Fish & Game, which has a hyper-local bend, but people’s opinions of it are very varied - whether on portion size, or value for money. There’s also a slew of other restaurants up there at lower price points. There’s also a farmer’s market on Saturdays until 1pm. And in Hudson, you can check out Olana (non-food).
Want to check out other places? Pine Plains - Dutch’s Spirits is a few years old distillery, and Ronnybrook Farm’s milk and products can be bought in the center of Pine Plains (as of 2 years ago; haven’t been up since) as well as many other spots in the Hudson Valley. If you don’t want to go to a farmer’s market, Adams (small supermarket with several locations) has a store in Kingston, a couple miles before crossing the bridge.
Wine: Definitely NOT an expert, and I prefer sweeter wines. In Pine Bush (a bit south of where you’re going) Baldwin Vineyards has some exceptional sweeter wines - strawberry and apple are my favorites.
Closer to the area of the Hudson Valley you will be in is Clinton Vineyards, in Clinton Corners, has some higher end dessert wines.
Links to 2 local (to me) wine trails:
Not sure why the wine trail page isn’t active, but it’s stored in archive: https://web.archive.org/web/20160322130352/http://dutchesswinetrail.com:80/
I tried to avoid seafood that’s easily available up in Maine, and the price point on some might be a little higher - there are numerous places that have burgers which are local, for example… Hope that helps!