It dawned on me the other day that I LOVE upstate NY so very much, and we spend tons of time up there in the Fall, but I have yet to create any substantial guides for all of you. I have a tab on my blog for our favorite NY spots, but it isn’t that clear about any specific Upstate NY destinations, so I really want to work on building that out this year, and making more detailed guides for anyone who wants to dabble in upstate! It’s a huge goal of mine so stay tuned!
This past weekend, we headed Upstate on Friday and returned on Sunday night. I’d always suggest taking the day off on Friday if you can, because the drive is WAY longer if you hit traffic around Queens. We left right after rush hour, around 10:30AM, and we didn’t run into any traffic. It took us about 2.5 hours to get to the Woodstock area from Long Island.
DAY 1:
1PM: Fishkill Farms – On our way up, we decided to break up our drive by stopping into an orchard. We originally hoped to stop into Lawrence Farms Orchard which is my personal favorite pumpkin patch/ orchard in upstate, but we had Claude in the car with us and they have a VERY STRICT no dogs policy. Do not try to bring your dog, they will turn you away! We ended up driving about 25 minutes across the river to Fishkill Farms which was just as beautiful! The market is very impressive, and we picked apples in their orchards, which has tons and tons of varieties! I think our 1 bag was about $10, plus $5 entry per person. The pumpkin patch is not super impressive, so I would only stop-in if apple picking is what you’re looking for.
4PM: Check-into our Airbnb – We love to stay around Woodstock, and the Airbnb we stayed at this time around was just lovely, plus they allowed Claude to come! It was a 3/1, and was about 15 minutes from Woodstock, Kingston and Phoenicia, so right in the middle of it all! We loved that they had a fireplace in the house, and a firepit outside, and we used both!
6PM: Dinner at R&R Taproom – We headed into Woodstock for dinner, but did not realize how insanely busy it would be, since it was a Friday and the first weekend of Fall. I’d HIGHLY suggest making reservations somewhere beforehand! We ended up at the R&R Taproom because it was a walk right in kind of place, but we ended up enjoying the meal. They had toys for Hudson, good beer for the guys, and the food was super fresh!
DAY 2:
9AM: Breakfast at Bread Alone – We had a Bread Alone right near our Airbnb, so we stopped in for breakfast. It’s never ever a let down!
10AM: Hiking at Lake Minnewaska – There’s a lot of carriage hikes where you can bring a stroller along! We actually forgot ours (parent fail) but we let Hudson roam around until he wasn’t having it any longer – so for about an hour. The foliage is AMAZING – I think the peak of Fall will happen up there in about 1-2 weeks, so around mid October. It was very beautiful now, but still not the peak!
1PM: Walk around Kingston – Kingston was hopping, there was a farmers market going on, and also the Phoenicia Flea! We stopped into Kingston Candy Bar and picked up some candy, and also stopped into Rough Draft Bar & Books which is a must-see. It’s in an early 1900’s building, and they have an entire kids section of books + tons of spec beers! We spent an hour or so here reading!
5:30PM: Walk around Woodstock – We headed to Woodstock for an early dinner to make sure we could eat somewhere nicer, since we didn’t have any reservations. We were able to get a table at Cucina, which we had been to once before and absolutely loved. They have a farm-to-table vibe, with mostly Italian food. We all split pizzas and a few pasta dishes, and it was so good. We all said it was hands-down the best meal of our trip! We walked around Woodstock at night after eating, and the temperatures were a perfectly chilly 45 degrees!
DAY 3:
9AM: Phoenicia Diner – It isn’t a true Upstate NY trip without a stop into the phoenicia diner. Not only is the food amazing, but the entire diner is decorated in the most perfect camp theme. The ceilings are wood and the bar has mid-century modern lighting. Every little detail of the diner was well thought out, and it is definitely the kind of place you’ll always be itching to get back to. I’d suggest getting there early, or expecting to wait!
12PM – Checkout – sad sad times! Some trips we’ll checkout and stick around for another hike, but it was rainy on Sunday so we ended up heading back. We got back to Long Island around 3PM, with enough time to grab groceries for the week!
I hope this itinerary is helpful to some of you, and I’ll be back with more upstate guides soon!
