48 Hours in Upstate New York
We took our little 5 month old, James, on his first getaway upstate to the Catskills. Whether you have kids or don’t, we think you’ll love this little weekend plan.
Hello our friends and fellow snackers… Madison here! We took our little 5 month old, James, on his first getaway. We didn’t go that far but headed upstate to the Catskills. While everything gets a bit more complicated with a small baby AND a crazy 6 year old vizsla, we had a lovely time. Honestly, whether you have kids or don’t, I think you’ll love this little weekend plan.
Friday
12PM — Departure
2PM — Sammies at Rossi & Sons
- Rossi & Sons
Some of the best we’ve had. Rossi & Sons is an iconic spot that has been open since 1979. It is family run and it feels that way. Go to the original location, but they also have a new market downtown or a shop at Marist University.
What to get: eggplant parm or any parm, the #4 on homemade focaccia, any special, Italian rainbow cookie.
4PM — Arrival at The Henson
- The Henson
The Henson is only a few years old but it’s a stunning inn in the quaint town of Hensonville near Windham Mountain. Now that ski mountain is private, so it’s less of a ski town and more of an escape. When I tell you they spared no expense with this spot — it’s a renovated old inn, but the decor and design feels elevated and chic. The rooms are a little small but they pull out all the stops: a mini crib, monitor, dog bed, mini fridge for breastmilk and everything we could ever need or want.
I wish we took advantage of the sauna and wellness room, but they have a pretty outdoor garden with fireplaces.
6PM — Dinner at Matilda
What to get: seasonal special, buvette steak, brick chicken, hazelnut tart for dessert, and pair with any natural wine.
Saturday — Day trip to Hudson
Hudson is a 25–35 minute ride away and worth the visit. I can’t believe I never explored this downtown, but it’s truly incredible. It’s way larger than you’d expect, with endless cafes, home stores, antique shops, and curated stores. If you wanted to, you could probably spend a full day bopping here.
10AM — Breakfast at Mel the Bakery
- Mel the Bakery
Mel the Bakery used to be on the LES in NYC (in the Elbow Bread space). It was so sad when they closed their bakery, but thankfully they picked it up and plopped it upstate with the same amazing quality bread and beverage program. This one has full curated grocery shelves, incredible matcha, tons of bread to buy, and of course PASTRIES!!!
What to get: weekend smoked salmon focaccia special, any croissant (we loved the jalapeño cheddar), oatmeal creme pie, cinnamon roll (made with croissant dough). If they have it, try the brown sugar matcha latte.
11AM–2PM — Bop around town
- Finch
Expensive but incredible home store.
- Maker Hotel
They sell their popular perfumes and candles + they have a cute cafe.
- The Antique Warehouse
A small drive from downtown but insane if you’re into antique shopping or furniture.
- Neven and Neven Moderne
2PM — Cafe Mutton
- Cafe Mutton
We ended up working up an appetite and snagged a spot at the ever popular Cafe Mutton. This has been on every top list, specifically one of the top restaurants in America by Bon Appétit. Mainly because of the stunning crispy, crunchy, sweet housemade crepes with maple syrup and oozing butter. You could say we liked them…
What to get: crepes, breakfast plate, radicchio salad, house made bologna sandwich, any special.
ALSO! They let our dog, Totti, sit inside, which was huge.
Other food options
4PM — Catskills town
We ended up stopping in the town of Catskills on the ride home. It has a cute downtown, but we only stopped to visit a quaint pottery shop. The pots in the window caught our eye and the owner herself was in there making mugs. It’s a great small business to support.
6PM — Dinner
Transparently, we had dinner at Matilda again due to our small baby needing to rest early. However, here are some other options…
- Deer Mountain Inn
A nearby inn in Tannersville with a quaint cottage like dining room.
- Stissing House
DYING to go here!! It’s a renovated house dating back to 1782 and it is supposed to be cozy with delicious simple food.
- Casa Susanna
Elevated Mexican food.
Sunday
Wake up and spend time enjoying The Henson’s amenities — the sauna, gardens, breakfast spread, etc. — or you can head to a nearby hiking path.
10AM — Paracasa
The hotel also owns Paracasa down the road, where you can try their award winning cinnamon rolls and an olive oil cake we loved.
15 minute drive… get more breakfast and cinnamon rolls at Fellow Mountain Cafe, OR…
12PM — Lunch in Kingston at Rosie
- Rosie
Kingston is a 45 minute drive and breaks up the trip a bit more. They also serve amazing baked goods — a theme for us ;). But don’t skip a breakfast or lunch sandwich on their homemade breads or bagels.
- Kingston Bread
Pretty well known and great for breakfast, lunch, or a treat.