facebook pixel

Presidents Day Weekend Getaways

Presidents Day weekend is coming up, and with the kids out of school for a few days, we normally like to get away for the weekend! When it comes to last minute plans, sometimes it’s easier to just get in your car, or rent one and drive, rather than fly! But if you can get a good price on flights, I’m all for it! Here are 10 destinations for the long weekend, and they are all within 5 hours of NYC!

presidents weekend


The Catskills

I think it’s safe to say that everyone knows what they are getting with a Catskills weekend away: An affordable trip with peace and quiet! This is a great trip to take with kids because the drive out there isn’t bad (around 2 hours) and you get to stay in cute lodges! Or a hotel, if you prefer. I would have to say this might be one of the best places to roast s’mores over a fire. If you’re looking for outdoor adventures for the long Presidents Day Weekend, New Yorkers love to head over to this natural beauty for travel plans.

Where to stay: The Graham

The Eastwind Hotel

The Hotel Dylan

The Roxbury Cottages


What to do:

Snowboarding and skiing is huge in The Catskills. There are plenty of mountains, black diamonds to ski down and, of course, lessons if anyone needs them! Another fun outdoor winter activity is tubing. My kids love snow tubing and I find it kinda relaxing to just sit on a tube and ride down a beautiful snowy mountain. Also, if you haven’t tried snowmobiling or snowshoeing, they have those there! It’s definitely more of an outdoor adventure place, so if you are looking to stay indoors, keep reading!

As far as finding great spots to eat, I’d recommend Phoenicia Diner, because how could you not love diner food?? They have everything and are focused on locally sourced products! Another great eatery is Brio’s Pizzeria, pizza is an American favorite. They’re not just a pizzeria, though, they are a full restaurant with a lot to offer, such as breakfast, amazing sandwiches like Nashville Style Hot Chicken for lunch and so much more!

presidents day weekend trips

Silvermine, Ct

Silvermine is a place I don’t think many people have heard of. It is located in Fairfield County, CT and named after the old legend of silver mines that were thought to be there, but never found. There a lot of history to this town and combined with the trails lined by beautiful trees, this town is not one to be missed! The holiday weekend is the perfect time to check out historical sites.

Where to stay: The Inn at Graybarns


Hotel Zero Degrees


What to do:

The Silvermine Arts Center is an absolute must-go. This spot is an exhibition and school all in one! They have drawing, print making, glass working, ceramics and so much more. I love places where creativity is welcome! Another fun thing to do is check out Grace Farms, it is an absolutely breathtaking public spot that was built with the humanitarian pursuit to peace. You can take a tour and look around the property. This really is the type of town where it would be great to fully commit to exploring the area and doing what the locals are doing, rather than touristy things. Finally, The Tavern at Graybarn’s is a farm to table restaurant, which is so cool, we don’t have too much of that near us!


Mohonk Mountain House, NY

This is an all-inclusive resort for both kids and adults AND its over 150 years old! So cool, right? They offer everything you can think of from their award winning-spa to special weekend events to ice skating and so much more! You stay there because that is where everything is, so you don’t even have to worry about driving around and finding things to do! This is an excellent destination for recreational activities and the main draw is the family-friendly attractions at this location just a short road trip away. Spending time together is our favorite thing to do and President’s Day Weekend is the perfect opportunity to do so.


What to do:

Let’s start with their spa, because why not? There is a full treatment menu, seasonal wellbeing collection, meditation, yoga and a fitness center! Next, you can take a hike or go ice skating, which my kids would love! They are great skaters and there’s something about finding a new rink that makes the experience more fun. There’s a ton of kids activities to look into, as well!

Finger Lakes, NY

Ahh the Finger Lakes, one of the prettiest getaways. It’s also a very romantic spot, if you weren’t aware. So if you’re able to get out of town, just you and your partner, I definitely recommend this area!

Where to stay: The Inn at Gothic Eves


Belhurst Castle

10 Fitch


What to do:

The Finger Lakes are known for being a popular place to visit in the summer, but what people don’t know is that it is just as cool in the winter. Have you ever been ice fishing? Well we can change that! I think that is really such a unique activity. If you’re in the mood to snowboard or ski, the Terrain Parks have you covered! They have lake snow effect there, so you are good to go! And of course, I could never forget to mention that the Finger Lakes have an entire wine region with wine tours. Yeah, you heard that right. There’s just something about enjoying a delicious glass of wine while overlooking beautiful snowy land. Finish off your trip by checking out the Corning Museum of Glass. There’s so much history, culture, science and technology to learn about glass. They have live demos and studios where you can learn

long weekend getaway

Montauk, NY

Montauk is an iconic spot in New York, located just past the Hamptons. This is also a great place to visit in the warmer months, but there’s no reason you can’t take a trip out there in the winter!

Where to stay: Gurneys

What to do:

There’s something about being near the water in the cooler months that is so calming. Gurney’s is open year round and has so much to offer! They have their own restaurants, a spa and even allow pets! The seafood is incredibly fresh, there truly is nothing like it! While this is more of a romantic, relaxing getaway location, you can totally bring your kids along!



Queens has a lot to offer! This is the closest getaway spot, which is perfect if you aren’t looking to go too far. It can be fun to plan a weekend jam packed with activities, but there’s something to be said about a place that has everything ready for you at your fingertips, with no planning needed on your end. Family Week is taking place the 19th-23rd where they will have family games, movies, arts and crafts, a roller rink and more! Check out their full schedule here.

Where to stay: The Rockaway Hotel


What to do:

The Rockaway Hotel has everything you need for the ultimate “staycation”.  To start with, the rooms are absolutely amazing! You even have the choice of bungalows, which are great if you have kids and want more space for the weekend! They have their own restaurant and rooftop to enjoy eating at, as well as cute local spots. Obviously, the spa is my favorite part! You can choose from a variety of facials and massages, including couples packages. What’s super cool, is that in the winter, they have outdoor saunas to enjoy! They also offer wellness classes, which is always a great option. It’s located right near the water, so if you want to take a walk on the beach, you can easily get there!

Cape May

This seaside resort town in New Jersey has plenty to offer in the colder months. Between the cute bed and breakfasts and the activities in the town, this is a sweet getaway for the weekend.

Where to stay: Beach Plum Farm


What to do:

Beach Plum Farm has so much to offer Cape May guests. Not only is it a farm that has their own market, but they happen to have the most adorable cottages on the property. There are several different types of cottages to choose from and they are great for the winter with their fireplaces. If you’re looking for a sweet, quiet getaway you should check them out! You can go on a farm tour, how fun would that be as a family? It’s a great place to make memories. The town itself is perfect to fully immerse yourself in, and do as the locals!

presidents day weekend

Woodstock, Vermont

My family and I recently took a trip to Woodstock, Vermont to go skiing and snowboarding, and I have to tell you we had an absolute blast! I don’t hear a ton of people talking about it and I must say this place is an absolute must-go! It is seriously the cutest town with fantastic outdoor activities, which is great for the winter.

Where to stay: Woodstock Inn & Resort

family friendly road trip

What to do:

The first obvious answer is to go skiing or snowboarding! The Inn is incredibly close to the Suicide 6 Mountain, making it an easy way to spend the day there. The views of the mountain are breathtaking. I love that the pool is indoor, so it can be enjoyed year round, as well as the billiards room! My son was loving that, and it turns out he’s great at it! We checked out The Red Rooster for dinner one night and it was fabulous! They serve breakfast, lunch and dinner, but I am raving about their seafood. You have to try the scallops! Another great place I recommend is Mangalitsa, they are a farm to table establishment, which I think is amazing. It is a smaller menu, but very much worth it. Quality over quantity!


We visited Boston a few years ago, and I have been meaning to go back! It’s one of the best cities to go to for the weekend, whether you’re taking your family or just your significant other, there is so much to do and see. We actually took the train out and it was totally manageable and only took a couple hours.

Where to stay: Hotel Commonwealth

long weekend travel

What to do:

We ate at Table, a dear friend of mine owns it, but being as unbaised as possible, my opinion remains that this place is the best! The set menu makes it so much easier and everyone gets the same thing, there is no plate jealousy! My mouth is watering just thinking about it. If you have your kids with you, check out the Boston Children’s Museum! It’s not only fun but educational, and it’s a great activity with children. If you’re a sports fan, Boston is a great sports city, there’s always a game to check out!


Philly is so close, you can easily take a one day or full weekend trip there! Ryder and I took the bus out there a few years ago and had a great day trip just the two of us!

family travel

Where to stay: Four Seasons Hotel Philadelphia

nyc road trips

The Four Seasons Hotels Limited, Philadelphia, Pennsylvania.

What to do:

Obviously, you need to get a Philly Cheesesteak when you go to Philadelphia! I recommend both Geno’s Steaks and Pat’s King of Steaks– I can’t choose just one! The Philadelphia Museum of Art is a must go, even if you’re with your children, they will love it! Another cool photo-op is the Rocky Statue. Betsy Ross’ House is a famous Philly attraction and in my opinion, something everyone should see. The very first flag was sewn in that house! The tour was incredibly educational yet so much fun.

This post was originally published February 11th, 2022*

For more travel posts, visit here!

travel quote

Pin it!

presidents weekend trips
long weekend family travel

Join The Conversation - Comment Below

17 thoughts on “Presidents Day Weekend Getaways”

  1. I love quick weekend getaways like this, too. We are staying home for the long weekend for Presidents Day but only because we just got back from 2 weeks in Florida for a family wedding followed by our week-long February break from school. I’m all about those cheap flights, too, but we aren’t opposed to driving up to about 12 hours if we have enough time.

  2. Well, I wasn’t planning on going anywhere, but I’d love to and what better time than a 3-day weekend. Thanks for the idea. 🙂

  3. I personally love the rustic feel of the The Graham and Co. hotel and of course, The Rockaway Hotel and Spa – i’ve heard so much about their services and their location is super nice.

Leave a Comment

Your email address will not be published. Required fields are marked *