If medical residency has taught me anything about life outside my training/career, it’s that I love maximizing my time off and exploring new places— even if “time off” only means having an entire normal weekend off (Saturday…AND Sunday? What a concept!)

Here’s our itinerary for our 2-day (very) mini road trip from New York City up to Hudson Valley!

2 Days in Hudson Valley New York

Day 1: Driving north through Beacon, New Paltz, and Kingston

Our trip started off with a departure from NYC as we drove north on the New York side of the Hudson River. This was my first time to Hudson Valley and I was pumped. Just breaking north of the White Plains region of Westchester allowed for the buildings to space out and trees to take over. We were surrounded by greenery even on the highway and I loved it.

Brunch and Beer in Beacon, NY

Our first stop of the trip was in the wonderfully adorable little town of Beacon, New York. The main street in Beacon is picturesque and the perfect representation of “modern quaint.”

We stopped for brunch at Beacon Bread Company along Main Street. Beacon Bread Co is a super cute space, with sea foam green brick walls setting a feminine backdrop to exposed copper pipes and bare bulb lighting. There is a bakery space in the front and lots of tables for food and merriment in the back. A customer favorite at Beacon Bread Co is the French toast made with in-house made brioche. I found the texture a little on the soft/mushy side, but the portion was huge and taste was fresh. We also tried the fried chicken sandwich with kimchi and gochujang, which I’d recommend.

Never too early in the day for beer…brunch in Beacon was followed by a brewery in Beacon. We made a quick pit stop at Two Way Brewing, which is actually owned and operated by the brother of one of Michael’s coworkers!

Brooklyn Cider House in New Paltz

After crossing west over the Hudson River, we made it to the next stop on our Hudson Valley itinerary: Brooklyn Cider House!

This cidery was recommended by a friend who made a similar trip up to Hudson Valley previously and I can safely say I agree with and happily forward this recommendation to you! Imagine sipping fresh hard apple cider and nibbling at an apple cider donut while seated at a shaded wooden table gazing out at the apple orchard to your left and a tranquil pond with stray apples bobbing at the surface to your right. That’s Brooklyn Cider House in New Paltz.

It was raining when we first arrived, but luckily the drizzle ended shortly after, leaving a comfortable cool breeze blowing across the orchards. The first thing you’ll see is the picturesque red barn-turned-tasting-room where you can sample ciders indoors and purchase apple-y gifts to bring home. I bought a jug of apple cider vinegar that is so perfectly housed in a glass jug and wax-sealed that I don’t know if I’ll ever have the heart to open it.

Proceeding further onto the property through the red barn, you’ll enter the literally picture-perfect outdoor area. There is a large open-air tent with wood fired pizza and burgers, along with 5 varieties of cider (my favorite was the wild-fermented raw, which was cloudier and funkier) and a cider margarita to choose from. We brought our food and drink to a table overlooking the pond and just enjoyed the peace.

Books, Bars, and Beaches Of Kingston, New York

Kingston was the original first capitol of New York, and dates back to 1652. It is an old and weathered but still cute little town. Our home for the night was located in Tivoli on the other side of the Hudson River so we only spent a few hours in Kingston.

Kingston, New York is home to an interesting historical landmark: The Four Corners. The intersection of Crown Street and John Street is the only one in all of America with all four intact buildings built prior to the Revolutionary War. The Matthewis Persen House, Dr. Matthew Jansen House, Kingston Academy, and the Franz Roggen House were all built between 1663 and 1775.

One of these buildings is now home to Rough Draft: a lovely bookstore/craft beer and wine bar/coffee shop combo. The airy feel, plentitude of windows, and beverage selection make it most definitely a place I would study at (with coffee in the afternoon bleeding into a beer in the evening…) if I were a Kingston local.

We took to Yelp to search for dinner and came across an unexpected but intriguing selection: Jamaican food! Top Taste Restaurant is a small almost cafeteria-style Jamaican restaurant that was ah-mazing. I won’t pretend that I can speak to the authenticity of Jamaican food, but I do agree with the online reviewers that the taste (and portion size!) at Top Taste are noteworthy to say the least. We tried the oxtail, curry goat, barbeque chicken, a side of macaroni and cheese, and a dessert of rum cake which was leagues tastier than the touristy ones we had in actual Jamaica. Other popular entrees we didn’t have quite the stomach space for included jerk chicken, red snapper, curry shrimp, and fried chicken. You choose from “medium” and “large” sizes, and I’d say two “medium” entrees makes for more than enough food to share between two hungry adults. Each meal comes with rice, cooked cabbage, and (my favorite) maduros fried sweet plantains. Top Taste Restaurant had no indoor or outdoor seating as of June 2021 (COVID times), but we planned to take our food to-go anyway.

We brought our food to eat while watching the sunset at Kingston Point Beach. Kingston Point Beach has non-porta-potty bathrooms and a semi-sheltered picnic area with lots of picnic tables. After eating, we lounged on a beach blanket on the sand and partook in some people-watching. We spectated a big party as they took off jetskis, while others splashed around in the water. I dipped my toes in the waves but couldn’t bring myself to go much deeper into the Hudson than that. The beach was fine enough, but we’re still talking about the Hudson River and the water was definitely dirty compared to other local waterfronts like the Jersey Shore. Our experience sitting on the sand at sunset was reminiscent of our time at Echo Lake Beach and makes me want to plan another trip to Maine…

Quirky Bed & Breakfast In Tivoli, New York

Suminski Innski is, in a word, quirky. Reviews online are very polarized, either glowing or full of repulsion. You have to come to Suminski Innsky with the right frame of mind and expectations, and it’s not for everyone. This space is not a hotel, it’s not curated, it’s not immaculately clean (or even thoroughly dusted, for that matter). But what this 1840’s Greek-Revival house is is a quirky and interesting space that is supremely fun to poke around in if you’re into that sort of thing (I definitely am). The decor could be seen as cluttered by one person, but lovingly inclusive by another. There are a lot of odd end furniture pieces and a pleasantly spacious wrap around porch full of mismatched rocking chairs overlooking the Hudson River, facing west to catch a perfect sunset. The clientele attracted by the Suminski Innski is just as interesting, and the space served as home to an eclectic mix of residents during the COVID pandemic, as documented here.

We booked the bottom floor suite complete with a kitchen and living room. That said, I wouldn’t plan on cooking in said kitchen unless you’re prepared to wash/sanitize the cookware and dishware. It seemed more decorative in nature and I was perfectly content to have the hanging copper pans and retro-style fridge just for the aesthetics. Additionally, the bottom floor suite actually did not have central air conditioning or even a window AC unit. Nonetheless, it did stay surprisingly comfortable with the help of a cracked window and a few fans already set up and circulating the air by the time we arrived.

Keep in mind there is a resident dog (a pittie mix, I believe), Milmo, who is very friendly and unobtrusive but does spend time indoors. He was actually the highlight of our stay at the Suminski Innski. He is one of the most mellow but friendly dogs I’ve ever met, and he actually just wandered into our suite, climbed onto the couch, and stayed the night with us. I can see how this environment can generate polarized reviews. Suminski Innski is old and unpolished, but also historic and very loved.

We awoke the next morning to the tantalizing smell of bacon. Breakfast at Suminski Innski is just as family-like as the inn itself. Cooked in a tiny closet-sized kitchen by the owner’s nephew, breakfast consisted of thick-cut freshly-fried bacon and sausage, pastries and bread from a local bakery, a veggie quiche, yogurt and fruits, and fresh coffee. I wonder how much bacon has seasoned those glass-smooth Griswold cast iron skillets hanging in the kitchen doorway.

Kaaterskill Falls Hike

Breakfast had fortified us and we were ready for our next adventure: hiking Kaaterskill Falls trail! Kaaterskill Falls is the highest double-tiered cascading waterfall in New York state and the hike takes you to three viewing areas: the lower falls, middle falls, and a viewing platform atop the uppermost falls. This hike felt more like a walk on well-trodden gravel rather than a wooded “hike,” but the walk quickly turns into lots and lots of steps (well-paved, sure-footed staircase made from carefully planted flat rock). I saw lots of people taking this trail in sandals, but there are obviously areas that get very wet (it’s a waterfall hike) so please be careful!

Kaaterskill Falls Hiking FAQ:

Where to park for Kaaterskill Falls hike?

Our hosts at Suminksi Innski informed us that the hike to Kaaterskill Falls used to be pretty quiet and secluded, but its popularity has skyrocketed since COVID indoor restrictions turned everyone and their mother into a hiker and outdoors-lover (not complaining about this!). Sadly, it seems that the increase in illegally parked cars from the onslaught of crowds coming to hike Kaaterskill Falls trail has forced the Town of Hunter to dramatically limit the areas you are allowed to park in. Please be sure to check out the most updated parking regulations at Kaaterskill Falls when planning your trip.

As of June 2021 when we visited the falls, the parking area at the lower falls was closed to limit the number of people walking along/across the highway to access the trail. The allowable parking areas included lots at Laurel House and at Scut Road. Other parking lots were located at North and South Lake, but those are further away from the actual Kaaterskill Falls so your hike will be longer if you park at the lakes.

What time to hike Kaaterskill Falls?

Kaaterskill Falls has exploded in popularity recently, in large part due to COVID-19 turning everyone into hikers. I would aim to arrive by 9:30am. The lot was 70% full at 9:30am on a Sunday morning in late June. By the time we were leaving around 12 noon, there was a line of around 15 cars waiting for a spot. There are also a few nearby homes renting out parking space for $10

How long is the Kaaterskill Falls hike?

The round trip (going in and then back out along the same route, not a loop) from the Laurel House parking lot is just around 2 miles. The total distance will be longer if you park at Scut Road or North/South lake, but all options are pretty doable for a part-day hiking excursion.

What direction should I hike Kaaterskill Falls?

I recommend starting with the descent all the way down to the lower falls, because more people flock there as the day goes on and it’s nice to beat the crowd. After you get your fix dipping your feet into the water, head back up those stairs (it’s a good workout) and stop at the Middle Falls. You feel like you’re almost in an open wide-mouthed cave with the tall narrow waterfall pounding its way down the center. Lastly, continue your way upwards to the Upper Falls viewing platform. You can also sit at the top of the literal waterfall, but be careful! There were multiple signs posted about the previous deaths that happened along this trail.

How difficult is the hike to Kaaterskill Falls?

The trail from Laurel House to the Upper Falls viewing platform is very flat, gravelly and extremely well marked/maintained. It’s almost shy of being paved, and a wagon or stroller with large wheels (to accommodate a bit of loose gravel) could handle it. We saw lots of people wearing flip flops (although I would recommend more sure-footed shoes especially as parts of the trail can be wet and slippery). The trail down to the Middle and Lower Falls is also very well marked and maintained, but has a lot more stones and steps. I counted 181 steps downward to these falls, and you have to ascend them to get back up to the trailhead. We shared the trail that day with plenty of families, with both elderly people and small children. You can do it!

Can you swim at Kaaterskill Falls?

You can get into the water, yes. The pools filled by the waterfalls are clean, crisp, and comfortable on an 80 degree day. The water isn’t deep enough to swim, per se. I was content just soaking my feet and taking pictures.

Alleyway Ice Cream

The day came to an end with a sweet treat at Alleyway Ice Cream, claimed to be “the world’s smallest and hardest to find ice cream shop.” Alleyway Ice Cream takes pride in its creative take on ice cream flavors. Interesting flavor examples include ube heath bar crunch, Thai tea cookies & cream, and sour cream blueberry. Count me in!