A Perfect Travel Itinerary for Cold Spring, New York - Travelerette

A Perfect Travel Itinerary for Cold Spring, New York

Cold Spring, New York is an itty bitty village about an hour away from NYC on the Metro North train. It is the home of some excellent hiking grounds, a young woman named Patience who has been friends with me since we were two, adorable antique shops, the world’s cutest B&B, and a weird professor I had in graduate school who really liked a paper I wrote on Agatha Christie, but thought my essay on Laura Mulvey was shallow. Some of these things may interest you more than others.

Cold Spring is an extremely popular weekend getaway with native New Yorkers and French tourists alike. If you like shopping, eating, and/or walking, Cold Spring is sure to have something for you too. Follow the following itinerary and you are guaranteed to experience the delights of Cold Spring.

Word to the wise: DO NOT attempt this day on a Tuesday, as both Boscobel and Hudson Hil’s will be closed.

Breakfast: The Pig Hill

Address: 73 Main St, Cold Spring, NY

The food to be found in Cold Spring and the surrounding Hudson Valley area is uniformely excellent. I’ve been told that this is because the CIA is in the area, but I thought the CIA was based in Virginia, and I don’t really understand why spies would make the food better. Are spies notoriously demanding customers or something?

Anyway, though I don’t usually bother to recommend hotels on this blog because I don’t care about hotels, I am willing to make an exception for the Pig Hill. The chef is CIA-trained, which means that he will be able to protect you in the night if ninjas attack. Also, he makes a mean omelet, which is my favorite way to start the day.

Pig Hill Omelet

There is also always a baked good of some sort to accompany the breakfast, like a muffin or scone or crumpet or whatnot.


On top of these breakfasting wonders, the Pig Hill has the best amenity of any hotel I have ever stayed at. Some hotels have free cookies, some have free breakfast, and one hotel I’ve stayed at had free peanut butter and jelly sandwiches which was very nice. But The Pig Hill has a freebee that I can guarantee will make you want to go stay there right now.

They give you free PIE. That’s right, every day there’s a new free PIE and if you are staying there, you can just take some. If you have friends, they can come and take some. I’ve had pecan, pumpkin, apple, lemon meringue…it was all amazing and cost me zero dollars.


You can’t have the pie WITH your breakfast though. Save it to enjoy with a cup of tea after dinner.

Morning: Boscobel

Address: 1601 NY-9D, Garrison, NY
Hours: 9:30-5 Every Day, But Closed Tuesday

Price: 17 American Dollars


Travelerette Tip: One of the most popular sights around Cold Spring is the historical Boscobel home in nearby Garrison, and the best way to get to Boscobel from Cold Spring, if you don’t have a car, is to take a trolley. This is an adorable green trolley that loops around the town and environs, eventually dropping you off at the historic Boscobel. You have to get the trolley at the bottom of Main Street, just by the Cold Spring train station. Take the 9AM trolley to Boscobel and the 11:17 trolley back to Cold Spring and following this itinerary should be a breeze.

Once you arrive, head to the visitor center and buy a ticket for a guided tour because it’s the only way to get inside. On the tour you will be presented with many fun facts about life in Colonial New York, but let me limit myself to…


  1. The Boscobel itself is a well preserved mansion that belonged to a Royalist named States Morris Dyckman–AWESOME name, BTDubs. When–SPOILER ALERT–the British lost the American Revolution, Dyckman had to hightail it back to the motherland of England for some time until the former colonies were no longer as angry with him for supporting King George III.
  2. Sadly, not all of the furniture inside the home is authentic to the period–many items were lost after SMD lost all his fortune and so the furniture had to be replaced with replicas. I know this because our guide would roll her eyes balefully every time she encountered one of these replicas placed around the home. In the Hudson Valley, antiques are serious business.
  3.  The structure of the house itself is gorgeous, but my favorite things were the hilariously stiff portraits of the Morris Dyckman family. Apparently the way American painters used to do portraits back then was to copy backgrounds from European paintings and then just plop a portrait of their subject in the middle of this other painting. I think it’s so funny that now many Americans are inclined to think of this country as superior to all others, but once upon a time we thought of ourselves as upstarts compared to the classier Europeans.


Lunch: Hudson Hil’s

Address: 129-131 Main St.

Hudson Hil’s is an extremely popular brunch place on Main St. back in Cold Spring. The NY Times wrote it up in their 36 Hours in the Hudson Valley article, and there is almost always a line to get in. Still, Patience and I only had to wait for about 30 minutes before we were seated. Bring a book if you don’t have a buddy to chat to.

Hudson Hil’s does a mean sandwich. I especially recommend their grilled Gouda sandwich with Granny Smith apples and figs. It is the perfect combination of sweet, tart, and savory and it comes loaded with fresh potato chips.

If you don’t mind having breakfast two times in one day, indulge in the scrumdiddlyumptious chocolate babka French toast.

I really thought there was no way to improve on regular old French toast, but this chocolate babka proved me wrong.

Travelerette Tip: If the line is simply aggrezh, just stop by the market and ask for a lunch box. Then you can have a Hudson Hil’s carbapalooza while you hike!

Early Afternoon: Hiking in the Hudson Highlands

After lunch, you’re going to want to walk off that Gouda/chocolate babka, so turn toward the mountains you will see all around you. (If you are on Main St, face the gazebo and turn right.) Now you will be heading right for The Hudson Highlands State Park.

This is an extremely popular place to go hiking. I always run into lots of French people when I am up here, so you know it is chic. However, you should be a little careful when hiking alone here, as my friend Patience warned me that sometimes bears are sighted in the area, though she didn’t know of any stories of people being eaten by a bear. This comforted me, as while being eaten by a bear does sound fun in an Oregon Trail sort of way, it’s not how I wanted to spend my vacation.

I strongly recommend hiking around here because the beautiful views of the Hudson give you the feeling that no time at all has changed since Henry first arrived. The Hudson doesn’t tend to show up on the “World’s Best River” lists, but I think it’s beautiful enough to hold its own with the best of them.


The trails have pretty good signage around them. Just avoid Breakneck Ridge unless you want a real challenge. People have definitely died hiking there, and that is not one of my attempts at macabre humor. It’s called Breakneck for a reason.

Late Afternoon: Shopping on Main St. in Cold Spring

Cold Spring spider

Not sure if the spider is for sale.

Cold Spring has some of the best antique shops in New York State. I bought a great old German advent calendar–complete with glitter on it that was still intact–at a stupendously messy but bountifully stocked shop on Main Street, and I bought a perfect pair of Bakelite earrings at one of the little vintage jewelry shops nearby. These are my special treasure because Bakelite was popular before pierced ears, so it’s hard to find Bakelite earrings I can wear. All the antique shops are on Main Street, so it is easy to find them.

If you only have time for three shops, let them be these:

  1. Swing, an adorable clothing store on 65 Main St. where I bought a beautiful clear umbrella that goes with everything.
  2. Old Souls, an all-purpose hipster hiking store on 63 Main St. that sells everything a hipster might need to go hiking or be a hipster.
  3. Rincon Argentino, an adorable Argentinian coffee shop on 21 Main St. that makes amazing alfajores, which are sandwich cookies of the Argentine.

When you are done shopping, take your wares down to the charming gazebo at the bottom of Main St and have fun watching people and/or the water. Then you will want to go back to the Pig Hill and eat your slice of CIA approved pie before dinner. There definitely won’t be room in your belly after dinner!

Dinner: The Valley

 Address: 2015 U.S. 9, Garrison, NY

The Valley at the Garrison resort is my favorite splurge restaurant in the Hudson River Valley. You can’t walk there from Cold Spring, so you need to hire a cab or drive yourself. Patience and I got there by engaging the services of an elderly lady who never gave me either her name or a smile, so we just called her The Grim Reaper, or Grimmy for short. But if you’re scared of Grimmy, just try Cold Spring Village Taxi. They have good reviews.

Once you have arrived at The Valley, your troubles will be over and your gastronomic delights can begin. The Valley uses only ingredients that are in season and, being as this was the fall, squash and game were on the menu. I started with butternut squash soup, accompanied by apple, chives, and speck.


I continued with a perfectly tender duck with plum, foie gras, risotto, and my favorite oyster mushrooms. I could probably live off those five foods for the rest of my life.


Dessert was my favorite part: pumpkin pie with sage butter ice cream and roasted pumpkin. I love the rich flavor of sage in a dessert and I am mad for roasted pumpkin. Also, I’d already had pie at The Pig Hill, so this was a two pie day and a two pie day is a blessed day.

Pie Valley

Finally, I was presented with these adorable little raspberry tarts to conclude my meal. They cost me as much as the pie did.


At the end of the evening I ran into some trouble because Grimmy had departed across the River Styx and  I found it impossible to catch a cab. I called for one, the hostess called for one, but apparently they were all booked up. One company said that they could give me a cab, but I waited and waited and couldn’t get any service.

Finally the hostess got fed up and offered to drive me back to my hotel herself. I accepted her very generous offer and we had a nice conversation on the way back. Seriously I think this qualifies the Valley for having the very best service of any restaurant I have ever been to. I’ve met some friendly waiters, but no one has ever driven me home before. Thanks, Valley Hostess!

And That is a Perfect Day in Cold Spring, New York

What would be your favorite thing to do in Cold Spring? Would you rather have pumpkin pie, pecan pie, a walnut muffin, chocolate babka French toast, or an alfajore? Also, would you rather break your neck or be mauled by a bear? Please leave your comments below!

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Who is the Travelerette? I am a native New Yorker who doesn't know how to drive or ride a bicycle. I speak French very well and Japanese very badly. In five years I have traveled in six continents, 26 countries, and 86 cities. My next travel goal is to visit all 50 states (and DC) in five years.

I am here to provide perfect travel itineraries with 24 hours, 3 fun facts, and 1,000,000 laughs! I hope that I can motivate you to get out there, see the world, learn something, and have a sense of humor about it all.
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41 thoughts on “A Perfect Travel Itinerary for Cold Spring, New York

  1. ROBERT LEE | Amazing Life Daily

    What you didn’t realize was that you were bugged as soon as you went to that restaurant with the CIA-trained chef. But then again, he was just doing his job to protect the country. LOL. Kidding aside, it does make for a good backstory, one that perhaps could aid in the marketing side, isn’t it?

    And oh, that was a good idea to take a hike. Indeed, the view is magnificent.

  2. Paige Wunder

    This does indeed sound like a perfect day! I would be ALL OVER that free pie. My husband doesn’t actually like pie *gasp*! But that just means an extra slice for me! Haha. Also, that beautiful gouda sandwich and homemade chips? That’s really my cup of tea. I LOVE cheese and I LOVE potatoes. Cheers!

  3. Alaine

    I am getting more and more curious with New York. I have never been to the US and I picture New York as what Sex and The City showed on TV. Reading your articles is like exploring New York on foot. I would really love to visit New York one day with my husband.

  4. Nina Zara

    Food looks delicious, i have nature in my backyard, so on a trip like this I definitely would hedonistically dig into food from pumpkin pie, pecan pie to walnut muffins.

  5. Bhushavali

    I haven’t been to USA yet and I really hope future has a trip in store for me!!! The food looks yummy, esp lunch looks awesome! The afternoon hike sounds like a perfect way to spend the day. Just enough dose of food and shopping and adventure! Thanks for itinerary!

  6. Kcalpesh Ajugia

    Your mention about you and “patience” having to wait only for 30 minutes was seriously witty. Looks like a perfect place to spend a day with a good breakfast, lunch, dinner and hiking around. Wonder why you didn’t post a pic of your favorite “hilariously stiff” portraits. 🙂

  7. cieri

    I havent been to New York and looks like there’s more to what I usually read about it. Thank your for yor tips which will come in handy when the time comes. By the way, I also do not know how to ride a bicycle. Lol! Just read your “About” description too.

  8. Me-An Clemente

    I’ve been to New York, but not Cold Spring. New York is definitely big. Last time, I went outside Manhattan too around Sleepyhollow. Anyway, hiking in Hudson Highlands seem quite lovely. I would like to try it if ever I find myself there. I also would like to try the chocolate babka French toast.

  9. Maaya Legaspi

    Living in a tropical country where there is no Winter or cold spring, I really thought what if felt like. Though seeing it in the movies makes me want to experience it firsthand. Also, this is great sight to see that you’re featuring other places aside from New York city where most people would like to see or read about. The food from the last restaurant you featured by the way looks appetizing. :p~

  10. Nadine Smith (Scenes From Nadine)

    Adventure, scenery, and food? That does sound like the perfect itinerary! Wow! The views from the Hudson Highlands are really something else! Even in the cold, it looks wonderful. I’m so distracted by the food posts though. They all look so good! The duck with plum, foie gras, risotto, and oyster mushrooms is making me so hungry. I love foie gras, risotto, and mushrooms!!!

  11. Tara

    Cold Spring is a fabulous little town, and the Hudson Highlands are probably my favorite place along the Hudson to hike. I haven’t explored many of the restaurants or shops, though. A fun read!

  12. Aika Loraine

    Yay! Cold Spring. Hmm. I am learning alot about places by just reading blogs. this post looks like a food blog entry as well. there were a lot of pictures of food! Boscobel looks a little creepy for me though. Well i can say that the architecture resembles houses i see when i watch Supernatural (the series, you know, sam and dean? hahaha). the sweets you are posting. makes me die of envy. im on diet!

  13. blair villanueva

    It seems that this part of New York will be enjoyable by walking alone, and have a distance to the busy and crazy city life. The mansion looks very interesting (can be a backdrop for winter ootd pic) 🙂

  14. John Rodgers

    Food looks so good, I can’t remember when I found good stuff like this. The town reminds me of times when I visited the many small towns of New York. Everyone thinks NYC when they hear the name of the state and truthfully the more beautiful parts of the state are to its north in the lakes regions.

  15. EG III

    A meal prepared by a CIA-trained chef is a great way to start the day. Was it a “killer” omelette…sorry I couldn’t resist haha 🙂
    As someone always looking for a challenge (and someone who has survived a broken neck–no joke), I’d be pretty keen to give Breakneck Ridge a go!

  16. Erica

    What a cute little town! Wish I’d known about it when I did my road trip in that area last spring. Boscobel and Hudson Hil’s both look awesome and now I’m hungry haha.

  17. Dariel

    This sounds like a very cool town with amazing views and so many different types of delicious food! I must make it a point to visit next time I’m in NYC!

  18. Cori

    It feels like every few months someone else I know has moved to Cold Spring. I used to explore upstate all the time when I was living in Rochester, but I really neglected it when I was living in Brooklyn — MetroNorth fell off my radar. On some future visit to NYC I’ll have to set aside some time to make my way back.
    Cori recently posted…A digital nomad’s guide to IstanbulMy Profile

  19. Marta S

    I’m so in love with your writing! And I’m falling in love with Cold Spring too, but it might be because of your writing too. It’s amusing and tranquil at the same time 🙂

  20. Gryselle Mae

    It is probably tough working for the CIA which is why the owner decided to set up a restaurant nearby for the CIA to relax and take some load off their backs while they munch on heavenly food specially cooked by the chef himself! Well, I’m just really guessing. Haha. 🙂 The food looks delicious and appetizing. Yum! 😀

    As for Boscobel, it may be a wonderful tourist spot but seeing the place gives me shivers. It is probably because of the design. It reminds me of a horror series I’ve watched before. Maybe they filmed the series at the exact same place?

    I’ll definitely order the babka in Hudson’s Hills though. Are those strawberries? Omg, yes they are! I can already imagine how it would taste like! <3

    The tender duck with plum seems kind of unique, don't you think so? I haven't really tried mixing duck meat with plums so I'm not really sure. Duck meat isn't so popular in my place and we don't really see it much often. I think I've only had a taste of duck meat one or twice for the last 28 years.
    Gryselle Mae recently posted…Roses De Chloé Perfume by Chloé: A Fragrance for WomenMy Profile

  21. Laura H

    Ohhh my gosh all the food looks insanely good! I have never heard of “Cold Spring” actually so I’ll have to look into it some more. This itinerary looks perfect for someone like me who likes good food and old buildings. Shame the furniture inside the mansion isn’t all authentic anymore 🙁 I also love that little fact about Pig Hill and the CIA – I’ll have to stay there to be extra safe! xD

  22. Tracy McConnachie Collins

    I have been to New York twice and although have travelled the east and west coasts have not really seen anything of the country but the big cities. I really will get a road trip (or preferably a train trip) sorted at some point.

    The food looks good. I do enjoy most of what I have eaten when in America though find the cheese never resembles anything vaguely like cheese as i know it! (Having lived in France who have superb cheeses!)Maybe i need to get out of the cities more! Now the pies…I could eat!!
    Tracy McConnachie Collins recently posted…My friend in Cape Town – South AfricaMy Profile

  23. Karen

    I loved this! I’ve been here once as a kid, so it’s nice to see the adult version of this. New York has SO many gems within train distance, so hopefully this inspires more people to leave the city. The food looks so good.

  24. Monique

    Looks like a fab day out with some delicious food. Glad you and Patience didn’t actually starve to death while waiting for the food to be served 😉
    Love to see more lovely places in and around NYC!

  25. Miriam Ernst

    First of all I love the way you write! Then, the food looks really tasty, I’ve been to NYC but never to Cold Spring, it looks like a great city escape and weekend getaway 🙂

  26. Ami

    Sounds like a perfect day alright. I would have loved to know more about Boscobel . It seems quite intriguing. The food through the day is yummy, especially the breakfast. Glad you had a good time.

  27. Shobha

    This takes me home! I grew up in Westchester and used to visit the Hudson Valley a lot before my parents retired and moved away. One of my friends got married in the area just to have the CIA cater their wedding. Beautiful part of the world.

  28. Brown Gal Trekker

    Never heard of this place but it sounds worth the visit! Love the food options! And the hiking trails are appealing. Next time I’m in the NY area, I’ll try to swing by this area and check it out. Thanks.

  29. Joanna

    Your post made me so hungry! I would go to that hotel simply for the fact that you get free pie! Also, it’s really interesting to find alfajores in this small town! I just returned from South America and ate so many, I love them, especially when they are covered in chocolate and filled with dulce de leche. It seems that a visit to Cold Spring will definitely leave you with a few extra kilos. 🙂

  30. Tracy

    I love pecan pie! But to receive such generous offer in such situation…definitely beat all those pies. Ha..You must be very glad. I can’t imagine if I were you in such situation. -.- I would have given her a big hug!

  31. Thuymi Do

    To be honest, I have been to NY several times and not heard of Cold Spring. But pictures of all that dessert has got me putting it on my list for my next adventure there later in the year! Thanks so much for the post!

  32. Yan

    I didn’t think there was a place in NY with hills and greens, thought it’s all tall skyscrapers and a congrete jungle. Nice travel itinerary, those who adhere to this guide will definitely not go hungry! 😀

  33. Aica Batoon

    Wow! The food there looks so delicious. Going to New York is a part of my bucket list and I’ll be sure that this city is the first one I’d go to if I had the chance. This really sounded like a perfect day! Thank you for sharing this travel itinerary. <3

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