Vacation Photos: Woodstock, NY

Last week, we escaped to Woodstock, a charming town two hours north of New York City. And we realized that the secret to a great family vacation is…

…having more grown-ups than kids! My mom joined us on the trip, and it was awesome to have a ratio of three adults to two children. That way, it felt like a relaxing vacation, versus a business trip:) You could actually steal moments for yourself, read a magazine, stare at the trees, spend one-on-one time with each child. We were so grateful to have her!

We also realized that a second baby is officially one million times easier than a first. Three years ago, when Toby was born, we also took a trip to the Hudson Valley, but we were totally frantic. Honestly, we were basketcases and even took him to the emergency room one afternoon for basically no reason. With Anton, we were so much more relaxed—my level of parental anxiety is 1/100th what it used to be, thank goodness—and Anton was happy to go with the flow. Parents of two, don’t you agree that it seems so much easier, emotionally? (The title of this book made me smile.)

Anyway, we were lucky enough to rent a farmhouse in Woodstock from a friend of a friend. Toby spent hours every afternoon splashing in the pool, Anton gazed up at the trees from his bouncy chair, and we picked tomatoes from the garden for dinner.

We also discovered an awesome wooden playground at a nearby elementary school, where we headed every morning with coffees and croissants. The maze of tunnels, bridges and forts inspired lots of pretend play. Over the course of the week, Toby was an airplane pilot, a bus driver, an ice-cream man, Mick Jagger, Keith Moon and a librarian.
The hippie town of Woodstock was so colorful and friendly! Every day we stopped by a little toy store, got lunch and then splurged on ice cream. (Salted caramel was the crowd favorite.)
On our last day we went on a more ambitious adventure. First we got lunch at the Rhinebeck Farmers’ Market and then went to the Old Rhinebeck Aerodrome for an old-school air show. Toby liked the planes although at times they were a little too noisy. :)
At night we would just chill at home, grill steaks and drink rosé (which I’m totally into these days). I’d definitely recommend the Hudson Valley if you’re in the mood for a relaxing trip with delicious food and beautiful scenery—the towns of Woodstock, Saugerties, Hudson, Tivoli and Rhinebeck are all charming. (There are some tips at the bottom of this post.) We’re already planning our trip for next summer. xoxo

P.S. Five getaways from NYC.

  1. to answer some readers’ questions: I am breastfeeding Anton exclusively; I sometimes have a small glass of wine in the evening after he goes to bed since I know I have 5-6 hours before feeding him again so the wine will definitely be out of my system by them. thanks!!!

  2. Instead for looking around for the top extended stay hotels in NY to spend in the vacations, Woodstock will be an amazing travel destination.

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  4. Woodstock is indeed a charming town nestled in the neighborhoods of the New York city, with the lovely places the amazing environments and the busy city services. Also another neighboring city the Manhattan is one of the topmost in the holiday destinations.

  5. So funny!! Toby and his daddy have the same grin. Cute!!

  6. So funny!! Toby and his daddy have the same grin. Cute!!

  7. Sounds so lovely! And I’m glad the second baby has been so much easier for you. I thought that would be the case for me, too, but unfortunately it hasn’t been. Wasn’t expecting colic, food allergies/ intolerances, and acid reflux. Now that he’s 4 months old, we’re starting to get things figured out a bit better and he’s starting to feel better, but it has been quite the test. Sooooo worth it though, of course!

  8. Such a wonderful vacation! Very nice photos. Perfect that it’s only 2 hours outside of the city~~ Love that you could pick fresh tomatoes for dinner.


  9. I also have far less anxiety and a much easier time breastfeeding with my second (9 weeks), but I found the transition to two to be much more difficult than I anticipated. My 3-year-old has been driving me crazy! I still haven’t found a new rhythm for the day-to-day. We do get out and have fun, but the house is a wreck and I forget to pay bills, and my freelance work is suffering. I think a better routine will start clicking when pre-school starts in 2 weeks. I continue to enjoy your blog. :)

  10. You saying about Anton watching the trees made me smile – my mum work with landscape stuff and has always been a big fan of trees to the extent that her mother used to take her out in the big old pram and she’d smile at certain types of tree and frown at others, and when my brother was little he would sit in his carrier by the back window and watch the trees sway but she must have talked about them constantly to him because his first word was tree!

  11. Looks like it was a wonderful family vacation! We were there earlier this summer, and I just did a post about Woodstock, too!

  12. I loved following along on Instagram – what farmhouse made my jaw drop! And you are so right, both about the second baby being easier and about needing to outnumber the kids on vacation. We just got back from a big family vacation in South Carolina, and our house had two small infants (under 3 mo), two 2-year-olds, and three adults (my sister’s husband couldn’t make it). There were other adults nearby if we were in a pinch, but on the whole, NOT relaxing!

  13. Joanna, It’s so good to hear that about your second child is easier! I’m convinced my baby is the most difficult child ever, but perhaps it’s a first time parent thing? I went through the ringer last week with her first fever – imagining every worst case scenario. My hubz and I are convinced we couldn’t handle another one. You give me some hope!

    Cheers! from,

  14. Whoa, you have FIVE TO SIX HOURS after you put him down? I am so jealous. My girl is 19 months and I don’t get that! I still sneak in a beer sometimes right after she goes down – my doctor essentially told me, “If you’re not tipsy, the baby won’t be, either,” on the theory that it’s all about whether or not the alcohol is fully metabolized. So I choose low alcohol beer and sip it slowly on a full stomach. Anyway, glad you enjoyed your trip!

  15. That looks like an amazing house. I’d love to see the inside – I think a home tour is in order. :)

  16. I love Woodstock! I was surprised to see long lost hippies sitting around the town when I visited – it totally lives up to the stereotype in the best ways. Such a cute little town.

  17. I love this post! Thanks for posting the link to that Book. It made me smile too. I have been on the fence about a 2nd baby. It makes me feel overwhelmed inside. Seeing you and your cute family adapt and grow makes me feel like “I can do it” too! :) My Little Boy Mason seems so similar to Toby. Makes my heart melt. xoxo

  18. The pics are lovely, but I’d really like to compliment you on your cheerful responses to the readers who immediately checked on whether you were breastfeeding your baby once they glimpsed a reference to wine in your vacation update. You handled their intrusive nosiness and implicit judgement with much more aplomb than I would have been able to muster. Bravo!

  19. 5-6 hours of sleep between feedings?! Please tell me how to do this! My little guy is 5 weeks old and the most sleep I get is 3 hours at a time. Sounds like Anton is a champ!

  20. Love these vacation photos. We’re buying a home this fall (hopefully) so I was thinking that a vacation away from New Jersey/New York would have to wait. After reading your post I’m thinking I can just drive and feel like I’m a million miles away from the every day craziness. Great pictures and great post.

  21. I love how little Anton always look so serious on the pictures Haha Such a cute baby.

    Greetings from Morocco :)

  22. Woodstock is one of my favorite places to visit. When I lived in Albany, I always dreamed of moving to Woodstock.

  23. These pictures are so lovely, looks like you all had a great time –
    PS: You should not have to justify yourself about drinking and breastfeeding

  24. I’m so glad you enjoyed your stay in the Hudson Valley! I’m originally from Red Hook (which seems to be where you took your family with little Toby:) and love going back to visit my parents and enjoy the scenery.

    If you’re ever in the area again, I recommend you check out Blithewood at Bard College (and the Fischer center!) and take a walk at Poet’s Walk. They’re my absolute favorite spots in Red Hook.

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  26. Lovely! In the future please pronounce Anton so I correctly pronounce it in my head. I so won’t check comments. Ton like downton? Like baton? Anyway, I just want to be saying right to myself. So silly, I know.

  27. it looks like it was a beautiful and relaxing trip! We definitely relaxed and enjoyed more with our second.

  28. I agree with you a million times over on the second child thing. I had so much panic and anxiety over our first-born. Our second baby was so easy and it was much more peaceful!

  29. kat, that’s so awesome! lizzie, i am actually breastfeeding. i would just have a glass of wine after anton went to bed since i knew i had 6+ hours before feeding him again (he goes to bed around 8pm and feeds again around 2:30am), so it would definitely be out of my system before he nursed. i actually looked up a whole chart about wine & breastfeeding online to triple check :)

  30. thanks for the sweet comments! the house isn’t actually a real rental house on airbnb or anything, unfortunately. we just rented it from a friend of a friend. they were doing us a favor since we had serious let-me-outs :)

  31. Looks fun! We have two girls and yes, I found the first baby a total shock to the system for a long time. When our second came, I felt so much more at ease with a baby and like I just knew what she needed. I felt like I was always trying to de-code every little thing with our first born. I would agree with you!
    And could Anton’s sweet bald round head be any cuter?

  32. looks so lovely. can’t wait to find out for myself that the second is easier than the first! and my Charlie has that same froggie puddle jumper. toby is so cute in it :)

  33. Hey that looks like a beautiful farm house. Is it on Airbnb by chance? I live in the City and am looking for a fall getaway.

  34. What a great looking trip! I’ve spent a lot of time in Woodstock, having attended undergrad in nearby New Paltz (which I’d also recommend checking out!). If you ever go back to Woodstock can get away for dinner for two, I highly recommend The Bear Cafe. I also hope you were able to check out the flea market over the weekend, if only for the people watching…

  35. You’ve got trouble on your hands if he is pretending to be Keith Moon…watch out for exploding toilets:)

  36. Love reading your posts.
    Beautiful babies.

    Are you using a Tula baby carrier? If so, how do you like it? My husband and I are thinking about investing in one, but having’t been able to read any real reviews…..


  37. I love the photo of you guys in the pool…takes me back home. How cold did the water get?

    -Kristin Hill

  38. How do you capture such great moments of Toby! Especially love his picture with the musician. :)

  39. that looks like the bestest kind of vacation! i have three little brothers and i’m sure the whole entire family would benefit from a week like that. thanks for sharing joanna! you’ve got the cutest babies:)

  40. I love these posts!

  41. Looks lovely! I agree that it’s more laid back with the 2nd little one. Although, for us, there were new challenges. The baby care seemed easy in comparison to balancing the needs of 2 kiddos at once. That was the adjustment for us! {or, still? 2 years later :)}

  42. Hi Joanna! I grew up in Rhinebeck, isn’t the farmer’s market fabulous? I also performed as a tween at the Aerodrome doing the Charleston with my dance class… ha! Anyway, definitely let me know your plans for next year- my family often rents our home and has lots of good connections for great vacays upstate. xoxo

  43. My good friends live in Wappingers Falls, and for a Michigan girl, it’s a very familiar feeling. I love going to visit the city and then spending some time at their home in the Hudson. She also has a shop in Beacon, Reservoir & Wood. Check it out next time you’re up there :)

  44. Looks like a wonderful trip! Thanks for sharing. My parents and I were just in Rhinebeck and Hyde Park for a long weekend–they visited the Aerodrome and loved it! The airshow sounded like so much fun.

  45. So glad you had a wonderful time. Love the gorgeous photos. Please, please do let me know where you got your shorts from – I love them!

  46. Beautiful! Also, I’m comforted to know that the second babe is so much easier! Our second is due very soon and I’m starting to feel pretty nervous :)

  47. I completely agree, Joanna. Your second is so much easier. When we had our third, it was like just inviting 1 more to the party!
    Thank you for sharing your beautiful vacation photos. We adore that area. Don’t forget about Phoencia! It’s a gorgeous little town with a really Main St. America vibe.

  48. Looks like so much fun and little Anton is quite the cutie! I’ve just started a blog myself, check it out? Thanks Joanna!

  49. It looks like such a relaxing place which is what vacations are all about! Glad you enjoyed your time there!

  50. Aren’t you brest feeding this time, Joanna? I’m brest feeding my second baby and it seems so much exhausting this time, but I know it’s worth it… a big hug from Buenos Aires!

  51. looks so amazing, glad you got to go!

  52. Lovely photos! You seem so relaxed and happy with your family :) I’m curious did living the “suburban” life for a week make you think of leaving NYC? I always fantasize about living in NY again but seeing photos like these makes me think maybe suburban living isn’t so bad after all. lol

    • Ack, say no to suburbs!!!!

  53. Your vacation posts are some of my favorites on this blog. :) Still referring to your Amsterdam posts for tips on my upcoming trip!

  54. Hi Joanna! Your photos + description of your days now has me yearning for a lovely vaca in NY. Perfection! We had our third baby 7 months ago, and I COMPLETELY agree with you about how much easier it is the second time around (and even more so the third time!). It’s increasingly more relaxed + even more fun :)) xo

  55. I guess you aren’t breast feeding :)
    Enjoy your wine! 9+ months is a LONG time.

    • Why put that smiley face after that statement?

  56. What a fun family vacation to wrap up the summer. Question – what kind of baby carrier are you carrying Anton in? It’s so cute!

  57. These photos are glorious! Thanks for sharing your well deserved and spacious family of four (five) getaway. Time to really enjoy the true luxuries of a nice full-of-stretch family home, even better in the rustic country.;) Anton now resembles Toby… those boys are enjoying each other. Thanks again Joanna; you all look wonderful! Be blessed.

  58. We had baby #2 a few weeks before you had Anton. I completely agree…this time around has been a breeze compared to last time. I feel like I’m able to enjoy this baby a little more … Last time I was so busy panicking over everything! Is she breathing?! Was that a cough?! We can’t take her outside!!!!…what if she gets sick? Or a stranger touches her? !!!! Ha. Oh man.

    Beautiful photos! You guys are pro vacationers.

  59. What a fun trip. :) You look incredible by the way!

  60. I’m so glad to hear someone say that going from one to two kids is not the nightmare that many make it out to be. My mom always said that going from one to two was an easy transition, but that two to three was hard.

    • my grandmother told us that two was a good number, any more than that and they outnumber you :)

  61. Some of my favorite childhood memories are at that wooden playground! All the scraped knees and splinters (you’re lucky if you avoided them!) their were always happy!

  62. What a sweet getaway! Glad you could escape the city and relax in the country.

  63. aww I have family in Saugerties, so I sort of grew up in the area. It really is stunning. Glad to see this area of NY getting attention on your blog :)

  64. What beautiful pictures of your family and vacation! Glad you had a good time. It is so important to get away and just…be. Cheers!

  65. looks like a perfect vacation!!! glad you guys had a great time.

  66. jm says...

    What a wonderful getaway! Looks as if you all had a great time. Love the pictures.

  67. What a wonderful family vacation! I was wondering what type of baby carrier you were using in the photo above? Is it one you would recommend?

  68. that caprese salad with orange (!!!) heirlooms looks like the definition of summer. so glad you were able to escape and really unwind. and your thoughts on child #2 make me less anxious for when we make that leap!

  69. Looks like a gorgeous way to spend time with the family! x

  70. Sweet sweet photos!

  71. I, too, adhere to the adults:children ratio (it’s a must!). The Hudson Valley is great. Looks like you enjoyed a wonderful trip with your new family of four! xx

  72. I’m from the Hudson Valley but live in California now – these pictures make me miss home! So beautiful! Glad you had a great time :)

  73. Looks like such a fun trip! What a nice, laid-back place to visit : ) I used to have a playground like that in my grandparents’ neighborhood, and I loved it. There always seemed to be great places to crawl and hide in there. I love that Mick Jagger was one of Toby’s pretends! : )

  74. Lovely vacation photos, Joanna! They’re so bucolic. A vacation in the countryside always make me fantasize about retreating to a tiny cottage to live forever! I’m sure I’d miss the city, but it’s a nice daydream :)