The Woodstock Era


Ok, not that Woodstock. I'm talking Woodstock, NY in the Catskills. (The concert actually took place about 50 miles south of this little town.) Skiing in the winter, hiking in the fall. While it might not be THE Woodstock, the little town does embrace its name.

Woodstock is a 2 hour drive from Manhattan. Just take a straight shot north and you'll find it. Nestled in the woods, just beyond the foothills of the Catskills, Woodstock makes for the perfect getaway spot for a reunion with friends. 

In early November 2009, Matt and I met 6 of our friends up in Woodstock for an awesome weekend of catching up, exploring and hiking. I say exploring because we spent about 2 hours looking for the trail head I picked out for us. Opps.

It gets cold up in the Catskills by early November, but we were lucky enough to have a sunny day for our hike. We did about 5 miles of the Jimmy Dolan Notch Trail to the Notch (3,200ft.) The first 1.5 miles were marked by woods and the occasional stream with a slight incline. The next 1/2 mile was a good climb gaining about 700ft.

It would have been a nice, not-too-challenging hike had it not been for the snow and ice that we met in the last 1/2 mile stretch. Some parts of the trail were very steep and the ice made it slippery and a bit treacherous. I breathed a sigh of relief when we reached the Notch and we were greeted with an amazing view:

The 8 of us rented this cute house for the weekend. It was really affordable (cheaper then most hotels!) and quite roomy inside with a great view off the back deck. We even got to do a little exploring in the backyard which seemed to go on for miles in the woods.

The town of Woodstock was really cute with great restaurants, little quirky shops, and a flea market filled with vintage and handmade treasures. It was easy to see why artists like Bob Dylan and Van Morrison once called this place "home." Mr. Morrison actually wrote the song, "Moondance" while in Woodstock.. pretty cool!


Even in early November, before skiing season, the restaurants were packed. During the day the town seemed so quiet, but at night we almost couldn't find a place to eat without a reservation! Luckily we did find an adorable French restaurant called Touche. It was delicious and I'm so glad they were able to accommodate our large group.


  • The Tea Shop of Woodstock- I picked up some amazingly delicious chocolate flavored tea in this shop. They also had the most adorable teapots and other little tea related lovelies.
  • Tibetan Arts and Crafts- Exactly what the name says.. I wish I could have bought everything in that shop. Amazing handcrafted items.
  • Keep your eye out for cute little antique shops scattered throughout the town.


  • Go hiking- Woodstock is just a few miles from tons of Catskills trail heads. If you want to take the Jimmy Dolan Notch Trail you can use a map showing the northeaster Catskills trails.
  • Ski, Snowboard, Sled- Hunter and Windham mountains are about 45 minutes away.
  • Wander through the town, shopping and eating.
  • Watch scary movies by the fire in your weekend rental house.. we chose The Amityville Horror which creeps me out to no end because I live 25 minutes from the real house. Freaky.
I really liked Woodstock and all the peace signs that were painted around the town. I'd definitely like to go back.. maybe in slightly warmer weather so we can do a longer trail!

Have you been to Woodstock or anywhere else in the Catskills?

(Some images are from me, some are from Cait, and some are from Niki!)


  1. Woodstock was one of my favorite trips. Surprising because it was so close and only a pair of nights. Magical place to spend with wonderful friends.

  2. totally! i was thinking the same thing.. i guess you don't have to travel across the globe to find some of the best adventures (although i'm all for that as well!)

    we have to do sunfish pond this spring/summer.

  3. wow i REALLY avoid pictures, huh?

  4. hahaha.. well maybe next time you should hike to the Notch then come explore the backyard with us!

  5. loved that trip so much! can you start planning us a spring/summer version??

  6. I loove the Catskills and Woodstock! These photos are great!

    My husband and I went to that area at the end of April a couple years ago. We camped (in a tent, while it poured rain and possibly a bear ran by...) in the Catskills. And then on our way out, we stopped in the town of Woodstock. Suuuuch a cute little town. I loved it. I'd love to go back sometime. Funny story though, at the time we didn't know that the Woodstock festival didn't actually happen in Woodstock. So we went around town asking people where the festival was held. They laughed at us and said it didn't actually happen there... Haha. So at the end of our roadtrip, we decided to drive through Bethel, NY on our way home where the Woodstock festival actually happened. We went and sat on the lawn where the concert was and it was pretty awesome!

    PS - What's the information on that rental house?? It looks awesome!!

  7. Oh, and PS - The comment you left on my blog about how a roadtrip traveling gave you the courage to quit your job... how inspiring. You are doing what you dream of now and that is something I really look up to!

  8. maybe next time i should actually bring my sneakers.

  9. haha, Anna.. I thought the same thing, I mean, why would they name it woodstock if it wasn't in woodstock!?
    sometimes it's a little scary to not have that safety net of a 9-5 job, but comments like yours definitely make me smile :) thank you!

    Alana... sneakers instead of brand new leather boots would probably be good haha