Catskills + Hudson Valley

I know every New Yorker has already hiked the Catskills or planned a cute little daytrip in the Hudson Valley at some point in their lives, but I’m bored and have now been to this region ten times (including four overnight trips), so I have a few tips for anyone who might want some recommendations. I love the Catskills and the Hudson Valley. As someone who loves hiking and eating, I’ll take this region over the Hamptons any day. The Catskills refers to the mountain range on the west side of the Hudson River and is a haven for artists, musicians, and writers. There’s some good hiking here and the Catskills is probably one of the best places to visit in the fall. The Hudson Valley refers to the region right along the Hudson River and has a long agricultural history, which is why every single meal I’ve had in this region has been incredible. A car is pretty necessary because there are so many towns you’ll want to explore, so many hikes to start in the morning, and so many farm stands on the side of the road to pick up apple cider donuts. It’s a quick drive from NYC, just about three hours, so you can squeeze this into any weekend.

Stay

The most ideal place to stay is my friend’s cozy 2-bedroom cabin with a fireplace, wraparound deck, and second-floor loft. Anthony and I were guests last fall and I couldn’t stop taking photos. She and her husband bought this cabin in the middle of the woods and restored it beautifully. It’s surprisingly affordable to rent on Airbnb, but due to COVID-19, it’s not available until next spring — but bookmark it for later! You’ll thank me.

Since that cabin’s not available right now, the next best place to stay is a B&B in one of the towns like Woodstock, Hudson, Kingston, or Saugerties. My friends and I stayed in a fun B&B in Woodstock called Twin Gables of Woodstock. This three-story home, owned by a couple of artists originally from Brooklyn, was exactly what we wanted from Woodstock: tasteful but quirky décor, a meditation room in the attic, a fire pit to roast marshmallows in the backyard, and the ideal location right on the main strip.

Eat

You’ll eat well in the Catskills and the Hudson Valley. It’s almost impossible not to. Perhaps my favorite restaurant in this region is Miss Lucy’s Kitchen in the quaint town of Saugerties. I ate at this farm-to-table restaurant twice in one week just because everything is so well done, from the grilled hangar steak with carrot risotto cake, to the roasted duck breast. Call for reservations.

Other restaurants to try:

  • Silvia in Woodstock for innovative Korean-inspired farm-to-table food (thanks to a Korean chef!). I loved my grilled octopus with charred sweet peppers and mushroom lentil pâté with pickled vegetables. Definitely make reservations because this is one of the hottest restaurants in town. We made reservations but still had to wait about 15 minutes to be seated because it is that popular.
  • Backbar in Hudson for Malaysian-inspired small dishes. I loved the cumin spice tots and black pepper wings with fish sauce glaze.
  • Lunch Nightly in Kingston for sandwiches. I’m not even a sandwich person, but the turkey sandwich with cheddar, balsamic lettuce and pickled red onions on a kaiser roll changed my life.
  • Alleyway Ice Cream in Saugerties for really interesting ice cream flavors. Alleyway may honestly be the best ice cream I’ve ever had. They have flavors like ube Heath bar crunch, Thai tea cookies ‘n’ cream, and sweet corn. You can tell each ingredient is homemade with love.
  • Grazin’ Diner in Hudson for farm-to-table burgers. You know it’s gonna be a good burger when every single ingredient’s origin is thoughtfully described on the menu.
  • Wayside Cider in Andes and Brunette Wine Bar in Kingston are super cute spots to drink, depending on if you want cider or wine, respectively.
  • Kingston Bread + Bar in Kingston for your carb fix. If I were a local, I’d be picking up my pastries from here every week. They have a lot of typical Jewish pastries, as well as things like cardamom buns and baklava rolls.
  • Lis Bar in Kingston for wood-fire grilled meats in a cozy atmosphere and movie nights on Fridays.
  • Supernatural Coffee in Hudson for coffee and pastries. Perfect for a quick early morning breakfast if you need to rush off to a hike.

Hikes

Kaaterskill Falls might be my favorite hike in this region. There are two trails: an upper trail leading to gorgeous valley views, and a lower trail going down to a double-drop waterfall. It’s an easy hike and gets crowded early, so go before 10am to find parking. The lower trail has a staircase that gets slippery from the waterfalls, so just be careful.

Anthony and I tried to hike Gertrude’s Nose at Minnewaska State Park Preserve, but it happened to be closed that weekend, so we ended up on another trail called Millbrook Mountain. While it wasn’t the challenging, epic hike I was hoping for, the views across Lake Minnewaska are absolutely stunning, especially in the fall. Once again, get there early for parking.

While Breakneck Ridge isn’t technically in this region, it’s on your way back to the city and is still my favorite in the entire state. Quick, challenging, and rewarding, Breakneck Ridge will always hold a special place in my heart because it was the first hike I did in New York. There’s a vertical scramble that may seem intimidating but is actually quite doable if you’re moderately fit and flexible. Stop by the charming village of Cold Spring after. (While you’re here, of course check out Dia:Beacon and Storm King Art Center. I’m not gonna even bother writing about those — if you haven’t visited these obligatory art institutions yet, you’re doing New York wrong.)

Random Things to Do in Kingston (where I spent the most time)

If you’re into American history, Kingston is a fascinating place to visit. It’s pretty large compared to the other towns in this region. Kingston was New York’s first capital and was burned by the British during the Revolutionary War. You can see some of the original pre-Revolutionary buildings, as well as beautiful Victorian homes in the Stockade District.

Also in Kingston is a 2.3-mile railroad trail that follows a creek. It’s a nice way to walk through town, as it connects the waterfront to midtown.

Anthony’s former coworker opened up a bookstore bar called Rough Draft that has become the hottest place to hang out in Kingston. When you visit, you’ll see why. Housed in one of the historic buildings in the Stockade District, this cozy bookstore has lots of space for reading, grabbing a coffee or cider, and attending one of the many events they host.

Maine

Anthony and I were still in Ogunquit when we decided to book another trip to Maine just eleven days later — one last hurrah before summer ended. Of course, this was an excuse to return to Ogunquit and stay in the same B&B, but we also decided to finally visit the stunning Acadia National Park and foodie city Portland. While these two destinations are roughly three hours apart, visiting both on the same trip felt like a perfect balance. Here are my recommendations:

Stay

Because our trip was so last-minute, we only had a few options when it came to places to stay. Since we had just two days for Acadia National Park, we decided to stay in Bar Harbor, where the park’s main entrance is. If you have more time, I’d suggest staying in one of the charming villages in the southern part of Mount Desert Island. I would not recommend our B&B in Bar Harbor; nothing was terrible about it, but the dainty, dated inn did not meet my usual standard. However, I would highly recommend the chic Airbnb I found for our one night in Portland. This historic three-story home was built by a famous architect, and, more importantly, it’s just a few blocks from Tandem Coffee Roasters. Our room was spacious and stylish, and check-in was completely contact-free, which I haven’t encountered since our Airbnb in Berlin four years ago. Our Airbnb was in the West End, but if we return to Portland I might want to stay in Old Port, since most of the best restaurants seem to be there.

Do

Acadia National Park was obviously the highlight of the trip. The park covers almost the entire Mount Desert Island, the largest island off the coast of Maine. It’s been a while since I’d been to a national park, and I had forgotten how magnificent they are. We only had two days, and while you could easily spend a week or more there, you can also get quite a bit done in just two days. A friend generously let us borrow her park pass, so we didn’t have to pay for the $30 entrance fee. The first thing we did was drive up to Cadillac Mountain. I’m still amused that you can just drive to the top. What a view! Even though there were a lot of people, there’s so much space to freely wander and enjoy unobstructed views of the island. We even saw one guy sitting by himself, reading a book, and ignoring all the tourists gawking around him — goals!

After taking in enough views, we continued our drive. We learned quickly that any time you see a parking spot, take it. There are enough sites everywhere that any place you park will have something interesting to see. Keep stopping as often as you can because there are so many hidden treasures. Meanwhile, parking during peak tourist season is scarce, so take what you can get. We found a spot near Jordan Pond, a hypnotically clear lake with steep inclines on both sides. We didn’t have time to do any of the nearby hikes but did take a lifetime’s supply of photos.

Our only hike in Acadia was Beehive Trail, a short but infamously steep hike. I’ve hiked Breakneck Ridge a few times without any struggle, so I was feeling pretty cocky — until about halfway up Beehive. While most of the steep parts had ladder rungs that made climbing up pretty simple (especially since I’m flexible and, despite my short height, can crawl up like a gecko), one section had no rungs, so I was literally gripping nooks and crannies in the rocks to keep from falling from the completely vertical cliff. Something I always forget until it’s too late is that I have slight acrophobia. It’s the reason I can’t rock climb, even just two feet off the ground, and the reason I will never be able to do a handstand despite being able to do nearly everything else in yoga. For almost a full minute, I was frozen in my tracks, scared stiff. Fortunately, Anthony came up and climbed right behind me, making sure I wouldn’t fall backward as I continued up. When we got to a flatter section, fellow hikers who had been watching congratulated and informed us that we had taken the harder route. Apparently we could have avoided that terrifying part if we had just taken a more roundabout path. Darnit! That’s what I get for being cocky and rushing up without scanning all options first. Regardless, it was a (mostly) fun climb and the view was as gorgeous as expected.

In Portland, we didn’t do much besides eat, but one activity that we really loved was watching the sunrise from Portland Head Light. About a 20-minute drive from our Airbnb, this iconic lighthouse has lots of parking and a perfect view of the sunrise. We were amused by the row of professional photographers who got there before us.

Eat

Honestly, we had a pretty mediocre food experience in Bar Harbor, mainly because we had so little time. I was given many recommendations from friends but couldn’t try any of them because some restaurants were closed the day we were there, or I hadn’t booked necessary reservations. However, this was all off-set by the incredible food we ate nonstop in Portland. I would return to Portland just to eat. In fact, I would return to Portland just to eat at one specific restaurant: Eventide Oyster Company. This was the one place that everyone kept recommending, and I see why! On our first night in Portland, we went to Eventide around 5pm to put our name on the waitlist. What a joke. We were quoted a 7-hour wait time. Seven hours?! I’m from NYC and have never been quoted that long. So, the next morning, we went an hour and a half before they even opened at noon. I know it sounds ridiculous, but it was worth it! We made friends in line (with some folks from New York and New Jersey, unsurprisingly) and played card games on a nearby bench. We were seated as soon as they opened! This is how to do it. Forget dinnertime (unless you put your name down around 4pm and don’t mind waiting for their call much later that night). We had some of the best oysters I’ve ever had. Until now, I’ve only respected oysters from Galway. But this meal changed my life. In fact, as soon as we finished our first dozen oysters, I immediately ordered another half-dozen of my favorite, Johns River. Everything we ate at Eventide was phenomenal, from the fried oyster roll to the bloody mary cava cocktail to the oatmeal cookie pie. I still dream about this meal every few days, and if we ever return to Portland, I will be eating here every single lunch.

The second best place we tried, and another spot I would be eating at nonstop if we return to Portland, is Tandem Coffee Roasters. This former gas station and laundromat makes some of the best pastries I’ve had in a while, from a breakfast sandwich with chorizo and smoked paprika mayo on a homemade buttermilk biscuit, to a brown butter cinnamon bun with orange glaze. We ate our pastries on the bench outside for breakfast one morning, watching the line for Tandem grow and grow down the block.

Per everyone’s recommendation, we went to Holy Donut for potato donuts. This place, as all good spots in Portland, also had a long line going down the block, but we were able to avoid it by pre-ordering our donuts online. They have some interesting flavors, such as toasted coconut and sweet potato ginger.

Ogunquit

Maine has always seemed somewhat exotic to me, probably because I’m from Hawaii, the farthest state from Maine as possible. I’ve always had a desire to visit, fantasizing about steaming lobster in a quaint cabin we rented on the coast. Anthony and I even made friends with a couple from Maine on our Morocco trip back in 2017, and though they invited us to their riverside cabin in Edgecomb, we never made it up there. Maine always seemed just a little too far — if I was going to spend eight hours traveling, I might as well go to Europe, right? It wasn’t until COVID, when I was desperate for another road trip, that a friend informed me that a delightful beach town called Ogunquit is only five hours away from New York City. FIVE HOURS?! Our previous trip to the Finger Lakes took that long! I dove into research and could sense almost immediately that I would love it here. In fact, less than two weeks after our first trip to Ogunquit, we returned because we had so fallen hard for it. Here are some of my recommendations:

Stay

I honestly don’t know if we would have loved Ogunquit as much if we hadn’t stayed at 2 Village Square Inn. This impressive, three-story bed & breakfast overlooking the rest of town is easily the best b&b I’ve been to in the U.S. The owner, Bruce, was the epitome of a host, making each guest feel like part of a family. There are 17 charming guest rooms, and I was impressed by the detailed description of each room on the website. Both of the rooms on our two separate trips had direct views of the water, and I loved waking up to the sunrise — the first light to hit (continental) America! The rest of the b&b is just as lovely, from the heated saltwater pool and jacuzzi, to the porch with rocking chairs. Each morning, we found a different spot on the three-acre property and were given a laminated menu and dry-erase marker to make our breakfast selection. The food was as wonderful as I expected: French toast with berries on one day, scrambled eggs and hash browns with peppers another day. Bruce checked on each guest to ask if they wanted a refill on anything. Freshly-baked blueberry scones and cookies were individually wrapped and available throughout the day, as was local coffee in the lobby. I could go on and on about how exceptional 2 Village Square Inn is, but just take my word for it: Book this place and book early because it sells out quickly and is full of return guests who also know what a dream this place is. 

Do

The first thing you should do in Ogunquit is walk along Marginal Way. This 1-¼ mile winding cliff walk connected our b&b to Perkins Cove and is the most scenic way to get across town. There are 39 socially distanced benches scattered along the walk, and we appreciated the unending opportunities to climb down rocks to get closer to the sea.

Anyone visiting Maine for the first time should take a lobstering boat ride, so that’s exactly what we did. We sailed with a lobsterman and an extremely knowledgeable tour guide (as well as a few families with young children), stopping by various traps to haul in freshly caught lobsters. Lobsters are fascinating! We learned that “lobsters never die.” Basically, lobsters don’t age, they do not grow weaker, and they do not become infertile. In fact, they become more fertile in their old age. Lobsters can regenerate lost limbs and regularly outgrow their shells. Once their waistline feels a little snug, a lobster will shed its shell, pump itself full of water to grow, then harden its outside into a new shell. (This is where soft-shell lobsters come from; they’re lobsters caught during this molting period.) Lobsters that have just molted are at a vulnerable stage for about three months until their new shell grows. Since lobsters don’t have bones, they can shed and grow indefinitely. Maine has strict laws about what type of lobsters can be harvested; they must be a certain size, and cannot be pregnant. When our lobsterman hauled in a pregnant one, he threw it back out into the sea. Female lobsters carry thousands of eggs, so pregnant lobsters are much more valuable in the wild than on a dinner plate. To book a trip, just call FinestKind as soon as possible. They have multiple trips throughout the day, and other trips besides lobstering ones, but they were selling out quickly when we were there.

I wasn’t too eager about checking out the beaches in Maine (I’m from Hawaii, after all!), but when we first went to Footbridge Beach around dusk, I was in awe. After crossing a little wooden bridge over idyllic marshland that gave me flashbacks of Normandy, we arrived at the most expansive beach I’ve ever seen. With soft sand that reminded me of Lanikai, this wide, flat beach with a low shore is the perfect place for young children learning how to swim. It’s also much less crowded than other beaches in Ogunquit, and it was so tranquil walking along the water. We visited a second time in the late morning, and it was decidedly less romantic and filled with more families, but it’s so spacious that even then it was hard not to appreciate the beach. It’s best to either walk or catch the trolley to Footbridge Beach, as the nearby parking lot charges $25 for the whole day. If you get there early and leave before 8am, or come late, I think they stop charging for parking.

Eat

Obviously, we had to eat lobster at every meal. It was my first time in Maine! Our favorite lobster happened to be the first place we tried, and it also happened to be the cheapest. We ate at The Lobster Shack twice during their lunch special: $20 for two one-pound lobsters, corn on the cob, and coleslaw. Yes, you read that right: $20 for two really good lobsters. I have yet to see a better deal anywhere else. The casual restaurant is housed in a former shack that once stored traps, rope, buoys, and other fishing equipment for lobstermen.

Our b&b gave us a $100 gift certificate (see, aren’t they perfect?) to Ogunquit Lobster Pound, so we had two dinners there. On our first night, we went on a Saturday around 7pm. Big mistake. The restaurant comprises both an indoor space that resembles a gigantic log cabin and a vast outdoor area that reminded me of camp. But the size of the space didn’t matter; it seemed like all of Ogunquit was here for dinner. We ended up waiting an hour and a half to be seated. For the second dinner, we learned our lesson and arrived earlier (and on a Sunday) and were seated immediately. To order, we walked up to the tank and chose which lobster we wanted, then they cooked it and brought it out to our table. It was a fun experience and a great way to enjoy lobster. Random tip: Their free bread is phenomenal!

Another lobster spot we tried was Barnacle Billy’s, which seems to be on everyone’s must-trys. I preferred The Lobster Shack for its lunch deal, but this restaurant was more atmospheric because you can eat right on the water.

If, for some reason, you’re sick of lobster, Brix+Brine is a chic raw bar. Don’t forget that Maine is also amazing at oysters!

Quick Day Trips

About a half-hour drive north is Kennebunkport, the fancier version of Ogunquit. It’s where the Bush compound is, if you’re into that. We had some extra time so we drove up to have lunch at the famous Clam Shack. There was a long line, but the lobster rolls were worth it! Cheap parking is available in the lot behind The Clam Shack. Also check out Rococo for ice cream flavors like chai cardamom, goat cheese, and guava and Maria cookies.

A 15-minute drive south is Cape Neddick, a gorgeous little peninsula that houses the iconic Nubble Lighthouse. If we had more time in southern Maine, I probably would have wanted to spend a night on Cape Neddick!