A perfect weekend in the Catskills
a 48-hr guide to blissful loitering
Hello hello! I’ve been traveling the past couple of weeks, so in lieu of a recipe, I have something different for you: a lovingly written, long-experienced guide to the Catskills. This is where I spent Memorial Day Weekend with my fiancee Michaela, my best friend Amelia, and her girlfriend Doro. I highly recommend the visit if ya live nearby!!
My credentials:
Michaela and I have spent lovely time in the Catskills, enjoying ski weekends and weekend getaways, and coming up right after our engagement to soak it all in. We are actually getting married this fall at Scribner’s Lodge near the Catskills’ Hunter Mountain!
I’ve come up to the Catskills multiple times a year since I was 6. Amelia’s family has a house up here, and we went to a YMCA sleepaway camp nearby. We rode out a few weeks of quarantine here back in April 2020, taking long, cold hikes and bopping (masked) into bakeries. Amelia’s my consummate guide to this area - she easily navigates around without Google Maps, and constantly introduces us to new amazing spots.
This guide is certainly not comprehensive, but it’s surefire for a great weekend upstate :)
Note: This is focused around the Delaware County area (near Windham and Hunter mountains), as well as spots to go on your way to and from NYC.
Thank you to
for inspiring me to write an overly detailed weekend itinerary. I still think about her perfect weekend in Manhattan, whose title I lovingly thieved for this ‘stack.
Friday Afternoon/Night
If you’re driving up Friday, you’re going to want to leave early enough that you can catch dinner or hit a town on your way up. I’m going to list a bunch of options of places to go. You can hit these on the way up or way back, too, so don’t feel like you’re missing out!
If you only have time for an on-the-go bite, do the Moon Burger drive-thru in Kingston. Moonburger is my favorite vegan burger spot (crispy smash patty, fresh lettuce, crunchy fried onions), but also has beef burgers if that’s how you imbibe, plus milkshakes. They opened a Williamsburg location last year, but the OG is special!!
If you have a little more time, check out Kingston. In addition to Moonburger, there are great shops and restaurants around town. Rough Draft, a bookstore meets cafe and bar is pure MAGIC. Stroll through the stacks in their building that predates the Revolutionary War, pick up a weekend read, and dream about opening your own bookstore-cafe. Check out their Instagram to see if there’s any Friday night live music happening. Other favorite spots in Kingston are bluecashew for cookery and Lovefield Vintage for clothes.
Book dinner at the Community Table at Blue Hill at Stone Barns. Blue Hill is an epicenter of farm-to-table fine dining (watch season 1, ep 2 of Chef’s Table for the full scoop). The greatest tip I could ever offer you is instead of paying $500 per person for the main dining room, pay $125pp for the Community Table at Stone Barns. Michaela and I did Valentine’s Day dinner there this year, and have done lunch (even cheaper); the meal and service are truly incredible.
If you get here early, take a walk around the property and farm!
Fun fact, their head chef Dan Barber worked with a Cornell agriculture professor to develop the honeynut squash, which has been growing in notoriety in recent years. Barber wanted a butternut squash that didn’t need so much to make it flavorful. Dang did they deliver with the honeynut!!
Hang out in Woodstock. I’d save Woodstock for the way back, since it’s such a fun town in daylight, but you can also walk around and grab dinner on the way up. Get tacos and a drink at Tinker Taco Labs and eat outside by the creek. You can also scoop an excellent meatball sub from Sharkie’s across the street and bring it over.
Don’t miss walking around the colorful, music-forward town! The true Woodstock festival happened nearby at Bethel, but the town is true hippie vibes.
Walk around Rhinebeck. I haven’t spent as much time here, but it’s a lovely town, a little more bougie than crunchy.
Walk around Beacon. I also haven’t spent much time here, but have heard it has great food and the art museum Dia Beacon is very notable.
Saturday Morning
Ahhhh, a mountain weekend. Start your weekend in the Catskills with a coffee, a good stare at the mountains or woods, and a short walk outside whatever home or hotel you’re staying at. Take a deep deep breath - the air is so much better here.
Next you are going to hit one of the greatest farmer’s markets to ever exist - the Pakatakan market (open mid-May through mid-October). The liège waffles are a must - they’re hot off the iron, with sticky pearl sugar inside and optional Nutella and whipped cream on top. Get both toppings so you don’t regret not getting them all weekend.
Top off your waffle with a breakfast sandwich from the stand in front of the waffles (it’s the only stand that serves them), and then walk around the market. If you’re staying in a home this week, get dinner fixings. Steak or chicken to grill, the goods for a big fresh summer salad, a bottle of hard cider, and ripe tomatoes and basil for a caprese (you can get mozz at the grocery store).
If you’re planning on eating out tonight, get some snack items for your hike this afternoon - berries, bread and cheese. Inside the red round barn, stock up on maple syrup, local hard cider, and multiple jars of the mustard, which is the only mustard I keep stocked in our fridge. If you’re gluten free, try a scone - make sure you clarify GF! - from Meredith’s.
Go home and put away any wares that need refrigeration and marinate your meat if you’re grilling later.
Grab snacks, or a sandwich in town, because we are ready for…
Saturday Afternoon
We’re in the Catskills, so of course we’re going hiking. You can do a more intense hike, or you can do what we in the biz like to call a ‘nature walk,’ which is a flatter, shorter hike. As a former Wilderness First Responder certification holder, I urge you to take at least 1 liter of water per person, snacks, lunch (if it’s a longer hike), sunscreen, sunglasses, and a layer if it’s a chilly day.
Cell service in the area isn’t great, so put the exact coordinates of your hike in Google Maps before you get in your car.
You can check out AllTrails for longer hikes, but these are a few of my favorite shorter hikes/nature walks in the area:
Andes Rail Trail: This is a flat, fairly short nature walk. It’s 3 miles, but you can turn back earlier if you’d like. You’re not missing any crazy views if you do. The hike is filled with beautiful wildflowers you can gather for a bouquet, just check them carefully for ticks since the population has been growing due to warmer winters.
Note: This is in the same town as our next stop.
Pratt Rock Trail: This is a quick, albeit steep, hike that rewards you with excellent views. There’s also a bit of history here - “America’s First Mt. Rushmore” was carved into the cliffside so you can do some cool rockface exploring. Don’t go on a rainy day since the steepness + rain = slippery.
Note: This is the furthest hike from our last stop - 45 minutes.
Alder Lake Loop: I actually don’t think I’ve done this loop, but I’m 99% sure I’ve gone swimming in Alder Lake and loved it. The walk seems flat and enjoyable, but perhaps muddy on a rainy day.
Note: This is 34 minutes from our next stop.
When you get in the car after your hike, it’s time to do your primordial scream. Not sure what a primoridal scream is? I am glad you asked!! When you are driving through the stunning Catskills, wait until you get to a point where no other cars or people are around. Roll your windows down, stick your head out, and let out a gutteral, from-the-bottom-of-your-lungs scream. It is an incredible release. If you think I’m weird and don’t want to do this, just try and if you still don’t like it then you can feel vindicated, which is second only to feeling a great release!
All of the hikes I noted above are within a fine driving distance of Andes, my current favorite town up here and our next stop. Bop around town, specifically:
Hit up Sounds Good records - the owner, Greg, will give you recs and will play anything you’re interested in on their excellent speakers. He also has post-its describing the vibes for many of the records. I left with more records than I’ve ever purchased from a record store before. And I love them all.
There’s a very fun antiques and vintage clothing store down the road owned by a woman named Ellen. Ask Greg for directions. Ellen gave us mini old fashioneds in ornate glasses and was effectively our personal shopper for the afternoon!
Finish up with snacks and drinks at Wayside Cider.
If you are an Alison Roman fan, you should probably check out her store First Bloom as well - it’s 20 minutes down the road. The store isn’t really different from other produce and shelved goods stores. The highlight is the handmade labels from one of the early employees (you can enjoy it on a jar of their honey or a postcard), and knowing it’s a space Roman has crafted.
Saturday Night
Saturday night is about enjoying peak summer (or fall if that’s when you’re here). If you’re enjoying Wayside and want to make a night of it, eat there and play their lawn games! You can also bop to Union Grove Distillery in Arkville for drinks and their Italian-style pizza truck. For a special night out, book ahead for Brushland Eating House. I have not been here but Amelia has and raves about it. It’s family style, so it has dinner party with new friends vibes. The food is straight from the farm and is a reasonable $75pp for the meal.
If you are staying at a house, skip a restaurant and grill baby grill. Take out that meat you were marinating all day or scoop some hot dogs at the grocer, and make your big fresh salad. Turn your speaker up loud. Uncork your cider or crack open a local beer. If you have a baker in the bunch, make an easy berry crisp with big scoops of vanilla ice cream. Eat outside as the late sun sets. Look at the stars.
Sunday Morning
Sundays are about an early, but long and leisurely, drive home. Kick off with the best breakfast I have had in a while, Mornings. The Korean cafe and market in Arkville opened a year and a half ago and their sweet and savory options are incredible. The chocolate chip caramel miso quickbread is one of my best bites so far of 2025, and probably the best quickbread I’ve ever eaten in my life. Please get it.
Another option is Phoenicia Diner on your drive home. This diner has been around since the early ‘80s, but the current owner came in and gave it a bit of a Brooklyn-in-the-Catskills vibe and an incredible menu. It’s first come first serve, and sometimes is a bit of a wait. Foodwise, the pancakes are excellent and trout is a great local fish that you’ll enjoy if you’re into tinned fish (it’s not tinned but has that vibe).
Now you’re ready to head home. Stop at one or more of the towns I listed above from the way up, or go to Stormking if you want a full day of outdoors art. Get home early enough for a dinner at home, unpack your suitcase, light a candle, and relish in the great fresh air you got.
I hope this guide was helpful. LMK if you go and do any of these shenanigans :)
If you read all the way to the end, know that I love you,
Maddie
omg yum it’s like i can taste the waffles!!
Your writing made me feel like I was there, smelling, eating, and experiencing summer in the North-East. Almost, but not quite, made me miss North America. Thanks for presenting the goodness in the US.