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Oct 30, 2007 12:47 PM

From NYC to Canaan, New York (Upper Hudson Valley Help Needed)

Hello, chowhounders. My sister, her infant son, and I are driving from NYC to Canaan to relax at a local B&B. I've already made reservations for Swoon Kitchenbar for one night, but I'm interested in your suggestions for other meals, including:

- something not to miss on the drive up from NYC to Canaan for dinner
- any great sandwich places/bakeries/general stores to gather provisions for hikes
- any cute places for lunch in the Canaan area
- recommendations for apple picking
- recommendations for farms to visit, especially those that make cheese (I'm vaguely remembering a delicious Camembert from Old Chatham?)

I know this is a lot to ask about, and I'm happy to take any recommendations that you can offer. We will have my nephew with us, so any place should be baby-friendly.

Thanks in advance!


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  1. Old Chatham Sheepherders is the farm for cheese. Otherwise Chatham Village is full of cute restaurants. Our Daily Bread is the place to go for bread, sandwiches and soups. Just down the road south of Canaan.
    There's lots of apple orchards on Route 9 near Kinderhook and down towards Hudson, also over the Rip Van Winkle into the Catskills.

    3 Replies
    1. re: coll

      Thank you so much for your advice. It is greatly appreciated.

      1. re: gold75

        The Red Onion in Saugherties is a great dinner place.

        1. re: gold75

          You're welcome! If you're staying at the B&B we stayed at (guessing you are, I think it's the only game in town), the walls are like tissue paper and unfortunately the guy next door to us snored like a banshee without a minutes break all night!! Otherwise it's quite a nice place....just try to get a room with no one next door! Or I think they have bigger rooms in the barnlike structure. They had a really nice breakfast too.

          ......OMG I googled it to jog my memory, can't believe there's FOUR B&Bs in Canaan now!! We lived there for awhile (most of my family still does) and my husband went stir crazy and had to move back to civilization after a year or so. But don't mind him, it's like heaven up there as far as I'm concerned. It sounds like Silver Maple we stayed at, by the way.

      2. The perfect place to stop on your way there is Madalin's Table at the Hotel Madalin in Tivoli (Northern Dutchess County). The atmosphere is beautiful, the food is IMO even better than Swoon (I'm a big fan of Swoon too), and they do not take reservations, but it is never so busy you can't get in. If you need a place for Saturday lunch, Lippera's in Chatham is very good, or for a genuine old diner with good home-style cooking the West Taghkanic Diner on route 82 just north of the hudson exit from the Taconic Parkway is cheap and tasty, a cut above typical diner food. I particularly like their corned beef Ruben.

        1. I just noticed you also asked about apple picking. I would highly recommend Philip Orchards on route 9H in Claverack. 120 acres of orchard and a huge variety of apples in a beautiful setting. Check to make sure they are still open, as the season is ending. 518-851-6351.

          2 Replies
          1. re: rrems

            Rrems-- thank you so much for your suggestions. So incredibly helpful!

            Coll -- yes, we're at the silver maple but we're in one of the free standing structures (whew!). That's the only place they let you stay with the baby ... they must know of the thin walls!

            Thanks to all.

            1. re: rrems

              Philip Orchards was an incredible rec -- thank you! We were warned that it was too late in the season by the innkeepers and disuaded from others we met to even try, but Philip came through and we had a fabulous time.

              Swoon was also great. My scallops were tasty but my sister's pasta dish (mushrooms, goat cheese, and pappardelle) was so delicious that I was seriously jealous during the whole meal. And I had almost ordered it! ;)

              We also really enjoyed Our Daily Bread ... delicious soup.

              Thanks again, chowhounders!

            2. There are lots of cute places around New Canaan. if you are looking for a good resto in town, gates has good food and is child friendly, for an upscale type of place - I take my 3 year-old and 6 month old (on Main st). For breakfast you can go to Reed's Country Cupboard on Elm Street - it is at the end of an alley on right if you go up the street. Haven't been but heard great things about Blue Hill at Stone Barns in Westchester. Resto is tough to get into but there is a cafe where you can drop in. Also it is a working farm on the Rockefeller Estate so you can look at animals (don't know if baby is big enough). There is an apple-picking place in Bethel called Blue Jay Orchards. Also there is a really good sushi place in Norwalk called Little Tokyo. Take 123 out of New Canaan into Norwalk into an area called "Broad River." The resto is in a strip mall across from Uncle Joe's. Great sushi and I take my kids.
              Update: Ooops! THere is a maple inn in NC too so I got confused. Sorry!

              1 Reply
              1. re: rubyloo

                New Canaan CT? That's about 2 hours south of Canaan NY, just so no one gets confused!