Car Trip: Hudson Valley and Berkshires Edition

Updated: Aug 27, 2018

We had the chance to visit some beautiful spots upstate this summer, which would also make ideal daytrips or weekend excursions in the fall as well. We have just begun our upstate exploration (we love Beacon, NY ), and plan to venture up a few more times this fall; but in the meantime here are some highlights from this summer.

Skipping around Boscobel House and Gardens in Cold Spring, NY


Indian Ladder Trail, Vorheesville, NY

Every summer, we visit Curious G’s uncle and aunt in Albany and take a few daytrips to the neighboring towns. This year, we took a hike in Indian Ladder Trail and got to see Albany from above. The terrain was diverse, yet easy enough to manage with a toddler (if you’ve ever shepherded a child down subway stairs while clinging onto a foldable stroller, this hike would be a walk in the park…literally and figuratively), and we even cooled off in a limestone cave!

That white strip towards the back and to the left is Albany

All a pair of jelly sandals

Love a blue sky dotted with wispy clouds

Uncle Michael gawked at my "hiking attire", but I think it was representative of the level of difficulty of this hike! Lol...besides, I pretty much live in dresses all summer and I was wearing my rubber Birks

Curious G had fun "looking for fossils" along the way

Hey, we're in a cave!

Indian Ladder Farmstead Cidery and Brewery, Altamont, NY

After taking a hike in 90 degree heat, we needed a break. Indian Ladder Farmstead Cidery and Brewery was only about a 20 minute drive from the Trail (perfect distance for a tired tot to take a disco nap in her carseat). The picturesque farm and mountains in the distance serve as a stunning backdrop for weddings, and there was a rambunctious wedding reception brewing in the barn when we got there. Inside of the main dining area, there is a bar where you can sample their house made hard ciders and beers. A lively crowd was enjoying a live band playing 90’s covers when we arrived. We sat outside to enjoy our beers, ciders, juice, cheese plate, and pretzel with bier cheese. There was a play kitchen, ride on toys and an old tractor to keep Curious G entertained; but the best part for her was the store. I was tempted to buy everything for future birthday gifts because everything was so cute! But then I convinced myself that it was the beer talking and reeled myself back in. We left with just a talking stuffed Audubon bird and a jar of blueberry preserves. There was a little menagerie of farm animals behind the store where kids were invited to interact with the animals, but we skipped that part.

This plum flavored hard cider was delightful

This giant pretzel was the perfect beer / hard cider snack

Feeling overwhelmed by the cuteness overload in the little country store

Berry picking anyone? These rows of raspberry bushes were ripe for the picking

The Cuckoo’s Nest, Albany, NY

We had dinner at The Cuckoo’s Nest that night and the food was delicious. I would return for the fried chicken. I don't have many photos from that meal because the lighting in the restaurant was more conducive to chowing down in a relaxing atmosphere and less conducive to getting good pictures. I also didn't think that I would be writing this post as I was savoring each bite of country fried yumminess.

The Olde English Pub, Albany, NY

We love this spot for brunch. The portions are generous and the patio in the back is oozing with charm.

The Olde English Pub is located in the historic Quackenbush House built in the 1730's. This English phone booth was not around in the 1730's but it jives with the whole old English theme

Another fun element ...people usually hop into this tub after knocking back a few

We had the bar to ourselves...maybe because it was a thousand degrees outside and everyone was hiding inside. We actually ate our large plates of brunch out on the patio.

Emack and Bolio’s Albany, NY

We have made it a tradition to come here every summer when we visit Uncle Michael and Aunt Mary. While we know that we can get the massive cones decked in rice crispy or froot loop treats filled with creamy cold ice cream at home in the city, we love the live music in the garden in the Albany outpost. They also carry an assortment of cute toys and gifts of the Melissa and Doug variety.

Slightly on the decadent side...

Hudson Hil’s Cafe and Market, Cold Spring, NY

Hudson Hil’s was recommended by more than one mom from a mom’s group on Facebook, and these moms know what they're talking about so we went with their recs. Located on Main Street, it serves up scrumptious breakfast and lunch menus featuring fresh ingredients sourced from local farms. I had one of the best plates of biscuits and gravy ever.

Crayons were procured for Curious G to use on her Polish coloring book

Split Rock Books, Cold Spring, NY

Main Street is lined with many cute shops for housewares, toys, bath and beauty items, and gourmet products. However, Split Rock Books stole our hearts with its outstanding selection of children’s books. And by outstanding, I mean thoughtfully curated and artfully selected. Curious G selected Coppernickel Goes Mondrian for herself, but I would have been hard pressed to select just one children's book to purchase.

Heidi, one of the lovely owners also gave us some recommendations for spots to check out in town including West Point Foundry Preserve, Little Stony Point, and Moo Moo’s Creamery.

We walked down Main Street to the train station (Where you can take Metro North from Grand Central), underneath and through a fun little tunnel and reached the Hudson River bank, where we stopped to watch a few boats sail by. After getting our dessert from Moo Moo's we parked ourselves on a bench right by the river’s edge and savored each sweet spoonful while enjoying the scenery.

Love this bookstore

One of each, please

Main Street

Moo Moo's is in the white house behind us. We were melting along with our ice cream in the heat. Shortly after this pic was taken, a friendly lady who was sitting next to us, knitting, shared a good portion of her life story with us. She was sweet.

Nice view for ice cream eating

Boscobel House and Gardens Garrison, NY

Boscobel was actually our plan C. We attempted to walk to West Point Foundry upon the recommendation of Heidi from Split Rock Books, but surrendered to the heat and wound up getting into the car to drive to Little Stony Point (also upon the recommendation of Heidi who said it has a cute little beach). However, Curious G fell asleep on the drive there, and stayed asleep when we got there; so we took that as a sign to head to Boscobel.

It was probably above 90 degrees when got there in the late afternoon, but it was still an enjoyable experience. The crown jewel is the Hudson River vista; and the gardens and orchards are lovely bonuses. We skipped the House portion because we prefer to skip air conditioned interiors on oppressively hot days. (I kid, of course)

This path leads to...

this Hudson Valley vista

Navigating our visit

Respite from the heat outside the museum design shop


Berkshire Botanical Garden, Stockbridge, Massachusetts

So this is technically Massachusetts, but it's only about a 20 minute drive from our friends’ house in Stephentown, NY, where we stayed one weekend in July. Three toddlers and their parents spent a lovely morning here exploring the grounds, playing in the children’s garden, hanging out with some cute farm animals, studying the fine art sculptures peppered in amongst the colorful blooms, jumping off large rocks, and enjoying a variety of sausages hot off the grill.

Running through the blooms

Lllama, Llama!

Countless cacti

Lickety Split, Williamstown, MA

Our plan to ride the Berkshire Carousel after visiting the Botanical Garden was thwarted by sleepy toddlers who tapped out in the car ride there. So, we continued on to Lickety Split instead and let them nap. I am including this ice cream shop in this post because we eat A LOT of ice cream and this was a standout. In fact, I still crave both Lickety Split and SoCo Creamery, which I also discovered on this trip. Luckily, Morton Williams carries SoCo, but I have yet to hunt down a pint of their salted caramel which is HEAVENLY.

Tanglewood, Lenox, MA

Tangelwood is an open air music venue in the Berkshire Hills of western Massachusetts. During the summer, it is the “home” of the Boston Symphony Orchestra. We purchased tickets for the lawn seats, packed a picnic and headed over for a memorable evening of hauntingly beautiful music, a casual dinner with friends on the lawn, and a view that will live in our memories forever.

The rest of my pics are of the kids pulling eachother in a wagon across the lawn and our picnic I will just leave you with this tranquil view

*This post was somewhat limited by my lack of descriptive photos. Please feel free to email me with any questions. I can also offer more recommendations in the Hudson Valley and Berkshires areas. is my email address.

50 views0 comments
Join My Mailing List
  • Grey Facebook Icon
  • Grey Pinterest Icon
  • Grey Instagram Icon