Girls Fall Weekend in Upstate New York {Full Itinerary}

This past weekend my girlfriends and I spent the weekend in Upstate New York to enjoy all the fall activities and scenery. This guide includes where to stay, eat, drink, explore, hike, and what to pack!

Where to Stay for a Weekend in Upstate NY:

We stayed at this Cozy 1800’s Farmhouse located in Saugerties, New York. The house had plenty of space for a group up to 10 with 5 bedrooms and 3 bath with all of the modern amenities including heat, wifi, etc. There is also a fire pit which you can use to make S’mores at night! (Just buy starter wood from local gas station). Cris, the host, was incredibly accommodating and even left us Apple Cider Donuts to enjoy + tons of recommendations for the area.

Girls Fall Weekend in Upstate New York

Weekend in Upstate New York Itinerary (3 Days):

Day One

Dinner at Dutch Ale House. They serve 16 draft beers with a focus on local ingredients. We ordered a variety of apps for the table and highly recommend the Smoked Japanese Sweet Potatoes, Spinach & Artichoke Dip, and the Potato Wedges. There were a variety of draft beers available to order including pumpkin beer and ciders. Prices are very reasonable in the $9-20 range!

Girls Fall Weekend in Upstate New York

If you still have room after dinner, head to Alleyway Ice Cream for dessert. They have amazing reviews online and I wish we could have tried but we were so full from dinner!

Hang out at the house by the fire for the evening and catch up with group!

Day Two

Kingston, NY

Start the day with coffee & matcha from Outdated: An Antique Cafe. The cafe was adorable and the cool thing about it is that EVERY single item is ON SALE – even the chairs you sit on! They were full of antiques and the vegetarian menu is all locally sourced & organic.

Girls Fall Weekend in Upstate New York

Explore the town of Kingston (New York’s first capital in 1777) and make sure to stop at the bookstore full of used books at an affordable cost. I purchased The Girl You Left Behind by Jojo Moyes and Lauren bought a ton of neutral coffee books for her apartment.

Stop for breakfast at Sissy’s Cafe with vegan, vegetarian, gluten free options incorporating local produce! I ordered the Southwestern Wrap with eggs, avocado, salsa, cheddar and black beans – so good!

Girls Fall Weekend in Upstate New York

Greig Farm

Head on to Greig Farm to watch/feed the goats, explore the pumpkin patch, walk around the market, and go apple picking at the orchard. We went too late in the year (Oct 16 weekend) for any apples to be left but if you go in September/early October you have a higher chance of success!

Girls Fall Weekend in Upstate New York

Tousey Winery

Drive over to Tousey Winery for wine tasting and lunch! We tried a mix of red and white and LOVED the Sparkling Queen which we bought some bottles to take home with us. The food from Clermont Cafe was delicious and the menu is constantly changing. We highly highly recommend splurging on the apple crisp dessert if available – it was perfectly crunchy and golden with warm gooey apples and ice cream to top. Always about the #balance!

Girls Fall Weekend in Upstate New York

Clermont Vineyards & Winery

Girls Fall Weekend in Upstate New York

Make another stop at Clermont Winery with amazing skyline views of the golden trees and mountains. They’ve been in the Hudson Valley since 2014 and produce a variety of wines including cabernet, chardonnay, and seyval blanc on-site.


Clean up at the house and head to Cucina in Woodstock for dinner! The food is contemporary Italian with a wraparound porch for outdoor dining. They also have picnic tables for warmer days in the front lawn. Highly recommend the Caprina Pizza with fig-rosemary jam, goat cheese, mozzarella, pear, & arugula along with the spinach ricotta ravioli with seasonal mushrooms. This was some of the best Italian I have had in a very long time, and the vibe was cozy and farmhouse chic.

Head back to the house afterwards for a bonfire S’mores night with your group! We packed all of the ingredients needed prior to arriving at the house to have ready for roasting. For a healthier S’mores option use Organic Graham Crackers, Hu Kitchen Chocolate, and Vegan Marshmallows (Non-GMO/Corn Syrup Free).

Girls Fall Weekend in Upstate New York

Day 3

The Mud Club

Start the day with breakfast bagels at The Mud Club. I ordered A Fool on Mill Hill which did not disappoint! I have a soft spot for breakfast bagels and the avocado, sprouts combo was so good! The trees were so colorful and they had festive decor for fall. We loved this spot and expect a line, but worth the wait!

Girls Fall Weekend in Upstate New York

Ashokan Rail Trail

Head over to the Ashokan Rail Trail in Woodstock for a scenic hike. You can walk/bike up to 11.5 miles but can tailor the walk to whatever distance you like. We walked 1 mile out and then 1 mile back. The views were incredible with gorgeous, colorful trees and a view along the lake. There are so many hiking options in this area, but we loved the views along this trail!

Girls Fall Weekend in Upstate, NY

Woodstock, NY

Head back to town for lunch and dessert. The Tinker Taco Lab was so cute and had a ton of outdoor seating.

Girls Fall Weekend in Upstate, NY

Finish off with cupcakes from Peace, Love & Cupcakes. If not hungry at the moment you can always purchase some to go! This shop WON Best Cake in the Country on Food Network, so we had to try! They had so many seasonal options including The Pumpkin Patch and The Spooky Ghost. GF options are available which I ordered the 99% Peanut Butter Brownie with Double Fudge Frosting. Hands down one of the best cupcakes I have ever had it was unreal!

How to Get Around

We drove everywhere which was very convenient for the weekend. We had no issues finding parking at every stop (just have some quarters on hand for the parking meters). If you do not have a car to get around you can take Ubers around which will be a bit pricier. Just make sure you have a DD for the vineyard tours 🙂

What to Pack for a Fall Weekend in Upstate New York

The weather was perfect when we visited in mid-October. Pack lots of layers and jeans, boots, booties, sweaters, vests, and light jackets. Also pack athleisure outfits for the hike! This sweater is from Amazon and only $29 which is what I wore in the pics above & love!

Hope you enjoyed this guide to a fall weekend in Upstate New York and enjoy your trip!! Leave a comment if you have any questions or shoot me a message on Instagram @thefitdelish.




hi, I'm Katya -- former D1 tennis player, certified CorePower Yoga Sculpt teacher, & soon to be IIN Certified Health Coach. Welcome to my page where I share all things wellness, real food recipes, and fitness. Thanks for stopping by and be sure to explore all things recipes, travel, yoga sculpt, wellness hacks, & shop all of my faves!


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  1. 12.12.23
    Kathleen said:

    Love this post, but you dont say what the house you rented is, or include a link. Looks perfect for our group of 7 women…. Many thanks for a link.

    • 2.8.24
      katya said:

      hi! having a hard time finding that listing now which makes me wonder if taken do. You can’t go wrong staying in Saugerties or Woodstock though! the full description of the listing was: ‘intimate cozy 1800’s farmhouse sleeps 10 guests saugerties’ vrbo if you’re able to have better luck than me. have a great trip!