It’s been a minute since I’ve been able to share travel guide and while things have already changed dramatically again since our weekend trip, I’m excited to share my Woodstock, NY travel guide today! This relaxing weekend trip in early November was the best escape out of the city after a stressful election week and it felt so good to be in fresh air (we had the most incredible weather!) and with my close group of friends.
The drive from the city is super easy and about two hours and was made even more smoothly thanks to Cadillac who loaned us an incredible car for the weekend! We had the XT4 model which fit all of us five girls and our suitcases perfectly. You definitely need a car when visiting Woodstock as Uber is rare to find so we’re so grateful we had an incredible car to get us everywhere safely that weekend! We’ve been upstate a few times but this may have been my favorite fall trip yet!
WOODSTOCK, NY TRAVEL GUIDE:
WHERE TO STAY
We chose this Airbnb because of the close location to downtown (about a 15 minute drive) and the great space. Our host was super sweet and left us champagne and appetizers when we arrived and it was such a cozy spot to stay for the weekend. It is an interesting location as it’s off the main road but we felt super safe and it was very quiet so that was the most important! Definitely recommend checking in while still light out as we had trouble in the dark finding it! Best part was the doors that opened out to the front yard and the big porch for slow mornings with our coffee. We stayed in our first night and ordered Chinese food and just caught up after missing months of girls nights!
WHERE TO EAT AND DRINK
Our first meal of the trip was at the Instagram famous Phoenicia Diner, which is about a twenty minute drive from Woodstock. Everything was outside due to the pandemic and they had cute picnic tables set up in the sun. The food was SO good and so worth the hype. Definitely a must to visit.
Once we arrived to downtown Woodstock, we stopped at this adorable bar for a happy hour drink and appetizer and it became a favorite of the weekend. It felt like you were in a treehouse covered in twinkle lights and disco balls with also the best cocktails. A great place to stay warm around the fire pits for an after dinner drink.
Next door to Early Terrible is their sister restaurant The Mud Club, which serves some of the best coffee and homemade bagels we have ever had. We stopped back both days and the staff was so nice as well. Make sure to order ahead for pick up as the line can be super long!
We came to this spacious restaurant for beers and snacks after hiking and it was a great spot to rest up. The menu features things like fried chicken, biscuits and fries so definitely was our kind of place!
For our one night out, we had dinner at Silvia and it was such a special and cozy meal. They had lots of outdoor seating with heaters and fire pits so we stayed warm while enjoying our delicious dinner of farm to table dishes and speciality cocktails.
On Sunday before heading back to NYC, we stopped in Kingston, NY which is about a twenty minute drive from Woodstock. We were sad to see unfortunately a lot of spots had closed due to the pandemic but we found this adorable breakfast spot that had some amazing sandwiches. A total win!
Another adorable spot in Kingston was this bakery right in their main downtown. I picked up a pistachio cookie and wish I would have gotten six more as they were one of the best cookies I’ve ever had! Just saw they are now shipping so may need to order some to have at home!
WHAT TO DO
Hike Overlook Mountain
We were so lucky with the weather and had almost a 75 degree day when we hiked Overlook Mountain the first week of November! This is definitely a steep and long hike but has gorgeous views and cool things to discover like abandoned ruins. Definitely recommend for prime fall leaf peaking!
Shop The Local Downtowns
We loved walking around downtown Woodstock to do some shopping from cool bookstores, gift shops and vintage stores. We also stopped in downtown Kingston as I mentioned and we thought they had really cool and unique shops to shop in as well.
For us, going upstate was about putting our phones down and finally getting a weekend to relax. Especially during a pandemic, we chose here as a safe and quiet place to be. It was so great to catch up on sleep and hang out with each other after one crazy year!