This specific itinerary is more tailored to visiting Kingston, New York in the Fall, but it’s truly beautiful here anytime of year.

Friday @ 3PM

Jump in the car, and drive up to Kingston. Depending on the traffic, this could take anywhere from 2-3 hours from NYC. Once you arrive, check into your super cute weekend spot, Hotel Kinsley. Hotel Kinsley is located in Uptown Kingston, and pays homage to the city’s storied past. Originally built in the 1860’s, the restored property was formerly the home of the New York State Bank.

Friday @ 6:30PM

After checking into your room, head downstairs and grab a drink at the bar. This cozy spot is perfect for discussing your weekend ahead. Try the Lost Weekend cocktail, it’s so refreshing and will instantly transform you into vacation mode.

Friday @ 8PM

For Dinner, make reservations ahead of time, but just walk a few steps into the dining room. Hotel Kinsley has one of the best dinners in Uptown. You can also try their sister restaurant, Lola Pizza, if you’re looking for a more laid back Vibe.

Saturday @ 8AM:

Wake up early and grab a quick coffee and breakfast at Outdated Cafe (Jonathan and I went here for breakfast the day we got engaged!).

Saturday @ 9AM:

Go hiking at Lake Minnewaska. We personally love Gertrude's Nose Loop, which takes around 4 hours. You can easily Hike to the cliffs, and turn around if you want a shorter hike. Sam’s Point is also beautiful. We usually grab sandwiches ahead of time at The Bakery or Russo’s in New Paltz. Once you find the most beautiful spot on your hike, take a quick break and fuel up.

Saturday @ 2PM:

Head back to Hotel Kinsley to freshen up, and spend the rest of your afternoon walking and shopping through Uptown Kingston. Hamilton & Adams has a great selection of men’s clothing and Upstate gear. Bluecashew Kitchen Homestead often does cooking classes, and we love browsing through all of their kitchen specialty items. And while there’s so many other great shops, make sure to stop by Rough Draft for a beer and book.

If you have time, there’s a few cute shops near the Round Out as well. We love Hops Petunia, Kingston Wine Co., and Clove & Creek.

Saturday @ 6PM

If you made it to the Round Out (which is the name for shipping area of kingston down by the water), grab a drink at Brunette Wine Bar for Happy Hour.

Saturday @ 8PM

If you’re OK with a short 20 minute drive, we’d recommend making reservations at Butterfield for dinner. Butterfield is located within the adorable boutique hotel, the Hasbrouck House (this could also be your home base for the weekend if you don’t mind being a bit in the middle of nowhere). Butterfield serves farm to table menus, changing with each season. During the Summer months, they also offer outdoor movies complete with fire pits, s’mores, and blankets. During the Fall and Winter, enjoy a drink in their game room after dinner. So cozy.

Hiking Gertude’s Nose at Lake Minnewaska

Sunday @ 10AM:

Enjoy a big brunch at Duo Bistro, or opt for coffee and pastries at Kingston Bread Co.

Sunday @ 11AM:

If you happen to be in town during the bi-annual Field + Supply fair, I’d recommend heading over to browse all of the incredible vendors and shops.

Sunday 2PM:

Check out of Hotel Kinsley, and pack your bags in the car. On your way out of town, head to Twin Star Orchards for apple picking, cidar tasting, and wood-fired pizza. You could easily spend a few hours here, enjoy!

Sunday 5PM:

Head back to NYC (with plans to come back to explore new Upstate getaways soon!)

48 Hours in Kingston, NY