I'd recommend the Terrapin or Gigi Trattoria in Rhinebeck for catering. I've eaten at both these places, and the food is delicious! In the Kingston area Duo Bistro and Bistro to Go are also great options. I haven't been to Swoon Kitchen or The Artists Palate yet.

Hi. The Bywater Bistro in Rosendale is a bit pricey, but the food is excellent. I had the best tofu sticks ever there. See my profile link to see photos. There quite a few good date spots in Saugerties, Fez Cafe, Land & Sea Grill Steakhouse, and Miss Lucy's. You have lots of options for romantic dining in the Hudson Valley!

Yum Yum Noodle Bar in Woodstock is delicious and has live music at night on the weekends.
Fez Cafe in Saugerties has great Morrocan/Mediterranean food. (Excellent chicken salad!) I tried Cinnamon restaurant, a new Indian restaurant in Rhinebeck, which was very good too.

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Yum Yum Noodle Bar
4 Rock City Rd, Woodstock, NY 12498

Have you tried Deising's Bakery in Kingston? I believe they make homemade donuts. It's a really old-fashioned bakery. During the Fall season, Adam's Fairacre Farms in Lake Katrine & Poughkeepsie sell cider donuts. I'm pretty sure those are made there. They are quite yummy!

Hi Jenn.
I'm intrigued by your post! I go to the Adam's Fairacre Farms in Lake Katrine, but I have never noticed or tried one of their cupcakes. If I see cupcakes like the one you described, I will investigate for you. Also, have you tried asking the folks who organize the Gardiner Cupcake Festival? I went to the festival in May to cover it for my blog. It was a great time! So many extreme cupcakes everywhere! Good luck on your cupcake quest!

I had a good experience a Angela's Italian Family Restaurant in Cairo a couple years ago. If you are into water parks, check out Zoom Flume too! (http://www.zoomflume.com).

I love Pizza & Pasta aka Capri! I go there about once a month when I travel from the Hudson Valley to Long Island. The exterior is very drab I know. Everything is good here! The salads are huge, wraps are very tasty, and my kids love the pizza. The service is great too.

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Capri
350 S Broadway, Tarrytown, NY 10591

I haven't been to The Local yet though a friend of mine raved about it. If you are looking for a supremely yummy place, I'd go to Le Petit Bistro. It is very cozy and intimate, and the French cuisine is really top-notch. It is a splurge though. $100 for 2 on average.

I'm counting the days until the Jolly Cow ice cream stand in Kingston opens again. Last year, it opened in late March. Another great place is the Coney Island ice cream stand in Catskill. I'm not a hot dog expert, but 5 Guys Burgers and Fries in Kingston has good ones, albeit greasy! Greasy, but good!

My favorite brunch places are Double O Grill in Rhinebeck, Cucina Restaurant in Woodstock, Mohonk Mountain house, Beekman Arms in Rhinebeck, Love Bites in Saugerties. Hype Park has a great diner, the Everyready Diner if you like comfort food.
You will find a bunch of Hudson Valley brunch ideas on my blog, http://www.hudsonvalleygoodstuff.com.