IMG_3811About two hours outside of New York, sits a charming artistic community nestled in the Catskills. Small shops and delicious restaurants line the downtown thoroughfare making it the perfect weekend destination.

This was a big weekend for us. This was our dog’s first camping trip!

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We adopted Riley’s last November when she was just 8 weeks old. She is a lovely mix of Lab & Hound and has made our little apartment a home. This photo is no joke. She was a picture perfect puppy who bravely faced the blustery cold of Brooklyn Heights in a little red sweater.

We have always wanted a dog to come along on our weekend adventures and Riley has proven up to the challenge! She was amazing this weekend and soaked up every minute of being in the Catskills.

Here are some highlights from our weekend away…


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Overlook Mountain is a great hike in that it offers great views and cool ruins while leaving you the second half of your day to further explore the area. The path is impossible to miss. It’s a large cleared out path heading straight up the mountain from the parking lot. Some people have commented that it doesn’t feel like you’re “in nature enough,” but once you get further up the trail though, it narrows and there are cool ruins of the old Overlook Hotel. There is also a Buddhist Monastery across the street from the trail head, which is definitely something to check out. 

The top has great views and picnic tables so bring a picnic lunch from one of the many local eateries. There is a large fire tower that you can walk up to see sweeping views. If you have a fear of heights, be wary for the tower often sways in high winds….!

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PRO TIP: If traveling with a dog, keep them on a tight leash. There are often numerous rattlesnake spottings a day on this trail. Keep your dog out of the low laying brush on the side of the trail. You don’t want your pooch to run into any trouble.

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Kaaterskill Falls is also a great hike to check out if you’re in the area. It’s much shorter and an easier hike, but beautiful and cool on a hot day since you’re walking along the water. It’s a bit of a drive outside of Woodstock but the drive through the mountains won’t disappoint. You can’t miss the trail head when driving along the scenic highway. It’s going to be on your right as you turn around a very steep bend. There is a parking lot a bit further up the hill, just be careful walking back down to the trailhead. The falls inspired numerous paintings by famous local painters and a poem by William Cullen Bryant. The time investment is minimal and the hike is gorgeous. The drive alone is worth it. 


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If you’re a fan of freshly baked bread and a good latte for breakfast, then Bread Alone is where you should head for breakfast. Their breakfast sandwiches are exceptional, using local produce on their freshly baked baguettes. They also often have a line as their lunch sandwiches are great as well, but the line moves quickly as your attention is focused on the amazing pastries in front of you. 

Bear Cafe – This place isn’t in downtown Woodstock, but just a short drive and it’s tied to the local music history. Bob Dylan and Janis Joplin’s manager opened the restaurant years ago, before it was taken over by some new chefs. It serves heartier fare. According to the Times, David Bowie dines there when he’s in the area. SOLD.

If you decide to take a meandering drive through the mountains, then head to Phoenicia. This beautiful little town is having a Renaissance if you will and is full of cute shops, local artists, and plenty of great places to eat. You definitely need to eat at the Pheonicia Diner, though you may never be hungry again.

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We spent the night at the Rip Van Winkle Campground. This place was right out of the movie “A Walk on The Moon.” People pull their RVs in and post up for weeks at a time. Kids are running around, families gather around picnic tables, it’s truly a little community at this campground. The facilities are clean and accessible. They have a local swimming hole on the property, a dog park (Riley’s favorite), and a small camp store. You can even get pizza delivered to your campsite and grab a dessert from the ice cream trolly……! (What?!)

We got a campsite on “Lover’s Lane” (hilarious), which was supposed to be more secluded from the rest of the campground and strictly meant for couples, but in reality it was just on a small loop slightly off to the side. The campground wasn’t anything to write home about, but did the job. We tend to enjoy campgrounds that give you more space between you and your neighbors, but for a last minute weekend away, it was all we needed.

We spent the evening, sipping wine in our hammocks by the fire, while Riley went to town on a bone we brought her as a first camping trip treat. Once it got dark, she was a bit on edge as tried to figure out where all the sounds were coming from. She only barked once in the middle of the night when another dog on the campground let out a howl, but we could tell she didn’t get much sleep. Too many things to guard us from as our little watch dog.

If camping is not your thing, I would highly recommend checking out The Graham & Co. This place is as hip as it gets and is truly a gem nestled in the mountains.

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Since we are all about making the most of our road trips, we often go out of our way to check out a particularly beautiful route or local attraction. On your way up to Woodstock, I would highly recommend taking a quick pit stop at Blooming Hill Farms. This local farm stand offers fresh produce, flowers, and lite bites from their eclectic little farm house. Once a month, they offer a farm to table dinner that is apparently not to be missed. You must reserve your seat at the table and then just sit back and let them serve you their delicious eats. It’s so popular that they have a “Supper Club” where you can sign up to receive a certain amount of seatings a year!

I picked up some fresh peaches and freshly squeezed lemonade at our stop which proved to be the best snack after a hike up to Overlook Mountain.


2 Comments Add yours

  1. Jessica says:

    I love this idea. Taking trips to explore near home…it’s perfect! The northeast in the fall is beautiful I’m sure and camping is such a fun way to experience that. Looking forward to more posts!


    1. Kate Bolger says:

      Thank you Jessica! I’m realizing that there is just so much to do in your own backyard!


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