How to Spend the Coziest Fall Weekend in Upstate, New York -

Upstate New York is the best getaway destination for a cozy, relaxing quintessential fall weekend. There are a variety of cities to explore when heading out of the city all about 2 hours away. In a past Upstate New York Getaway Weekend, we explored Saugerties and Woodstock area. This weekend in Upstate New York recap covers the Catskills area where we stayed in Livingston Manor, New York as our home base. Livingston Manor was the perfect destination with a lively town with an incredible selection of stores, and central to other nearby areas to explore! Recapping the exact itinerary we followed during our getaway couples weekend in Upstate New York.

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Best Time to Visit Upstate New York: We visited the weekend of November 15-17 which had amazing weather, however the fall foliage was not in peak state. Late September to Mid-October would be the best time to spend your weekend in Upstate NY if wanting to capture peak foliage. November was still great as we got all the fall, cozy vibes and it wasn’t crowded at all when visiting!

What to Pack for a Weekend in Upstate New York: Layers are always great during this time of year as it can get warmer during the day and chillier at night. I rounded up some of my favorite fall Aritizia finds and Amazon fall finds for some packing inspo!

Day 1: Departures & Dinner in Chester, NY

How to Get to Upstate NY: I absolutely recommend taking a car to Upstate so you can easily get around to all of the different towns, breweries, shops, towns, restaurants, etc. My best friend Lauren and her husband Tim were so nice to drive us up in their car. We left after work around 6PM to drive about 2 hours Upstate. If you do not own a car, you can book a rental here:

Where to Stay in Upstate NY: We stayed at this cozy Airbnb in Livingston Manor, NY. It had a total of 4 bedrooms, one of them being a loft with 2 twin beds. This was the perfect location with a rustic, lodge vibe and it also had a fire pit outside.

Hotels: If you choose the hotel route, I would recommend either Hemlock Neversink or Kenoza Hall which are both incredible and cozy boutique options for your getaway weekend in Upstate! I would generally recommend staying in a hotel when not traveling with a larger group.

El Zapata 3 Restaurant

Stop along the drive to Livingston Manor, NY for a bite to eat. If you can get out of the city early enough you could eat in Livingston for dinner, however the restaurants weren’t going to be open still by the time we arrived. Therefore Lauren found El Zapata 3 Restaurant along the drive in Chester, NY and we all agreed Mexican would hit the spot!

This was such a good hole in the wall find and they have almost all 5 star reviews. We ordered a variety of plates to share including burritos, enchiladas, guac, and fajitas along with some spicy margs and everything was delish. Would absolutely recommend if you need a good dinner spot along the way to your destination!

Day 2: Brunch, Livingston Manor Shops, Brewery, Cozy Dinner

Spend Day 2 in Upstate NY exploring Livingston Manor town and all of the unique shops! Finish your day with drinks at a gorgeous brewery followed by dinner and cocktails at a cozy hotel restaurant.

The Walk In

Start your morning with brunch at the cutest cafe, The Walk In. We arrived at 11am and just beat the morning rush to get a table! The breakfast biscuit sandwiches were heavenly along with their baked treats.

Instagram: @thewalkinmanor

Shop Till you Drop!

Explore the endless shops in Livingston Manor, each with a unique collection and charm. Every store was a blast to explore and these are all the ones we visited:

Life Repurposed: Massive antique store with fun rooms of a variety of old goodies
Long Weekend Catskills: Gorgeous home decor shop with Moroccan imported rugs. We met Ninze and another owner and they were both so sweet and fun to chat with!
Upstream Wine and Spirits: Fun liquor and wine store. We bought some fun bottles of mezcal and tequila from here. The shop owner was so sweet too!
Drooz and Company Catskills: Eclectic gift shop with an endless selection of fun items. We all found some great stocking stuffers here including bitter mixes for cocktails!
Concrete + Water: Seasons: Gorgeous selection of adult clothing, apothecary & candles, and lastly baby clothing/accessories. John bought a candle from here that smells amazing!
Corners New York: Modern art & design store with great selection of coffee table books, artwork, and some unique coffee makers John seriously considered buying.
Homestedt: Cozy country home decor, hunting, and fishing store. Great shop for the boys and Lauren also got a cute owl candle from here. You MUST visit this charming store during your weekend in Upstate, NY.
Nest Catskills: My favorite home decor store we visited. I adored her style and they also had a great selection of clothing and accessories. I bought a jacket from here I love.

Upward Brewing Company

Drive over to Upward Brewing Company with both an indoor & outdoor space. The outdoor space has plenty of tables and a few fire pits you can sit out admiring the views on the water. There is also a hike you can do if you are wearing the right shoes with supposedly great views at the top!

Happy Hour & Games at Airbnb

Head back to your Airbnb or home for a light happy hour and drinks while playing some games! Some of our favorite games include: Settlers of Catan, Who Am I (what we played), Scattergories, and Loteria (Mexican Bingo)! Shoutout to Lauren for bringing all the snacks and decor for this cozy setup!

Bittersweet at Hemlock Neversink

Drive about 30 minutes to the Hemlock Neversink hotel for dinner at their restaurant: Bittersweet. Bittersweet is a locally sourced, plant focused restaurant with a 3 course menu. The space is cozy and intimate with a variety of rooms with fireplaces and gorgeous rustic designs.

We started with shishito peppers and mushroom toast for the first course, squash risotto and steak for the second, and a delicious chocolate mousse for dessert! Each couple ordered one of each course so we could try everything. The lavender cocktail also hit the spot 😊

Day 3: Farm & Cidery, Brunch with a View, Relaxation Spa + Massages

North Branch Cider Mill

Drive 20 minutes away to North Branch Cider Mill in the morning for a cozy cup of apple cider and to explore their home decor and homemade goods. They also have a farm in the back where you can feed the sheep and goats! They have the same owners as the Homestedt store in Livingston Manor with an incredible selection of food, and cozy home decor. We left with so many goodies including mulled spices, apple cider donuts, honey, teas, and apple butter.

Seminary Hill

Continue on for about a 12 minute drive to have brunch at Seminary Hill, a hotel, restaurant, and cidery all in one! The space is open with a gorgeous view of the orchards. They also have an outdoor space with games, corn hole, and a fire pit. For any brides to be, this would also be a great potential wedding venue, the views were amazing!

Hemlock Spa @Kenoza Hall

Drive another 15 minutes to end your cozy weekend in Upstate New York with a relaxing spa and massage experience at Hemlock Spa. This is located in the gorgeous Kenoza Hall Hotel. The Spa has the coziest greenhouse ‘earthy luxury’ space with a barrel sauna, Kneipp sensory path, outdoor showers, cold plunge, cozy fire, hot tub, pool, and a variety of massage, facial, and body treatments. This was a heavenly way to end our relaxing couples getaway weekend!