The Best Weekend Escapes from NYC

Brooklyn Bridge - weekend escapes from NYC

Last summer, in the era we now call “pre-COVID,” I took my daughter to a nearby park in Connecticut where I live, and met a very nice, but very lost Italian family of 5. We got to talking, and the father shared that their original plan was to visit NYC, but sadly didn’t find it to their liking after a day or two. Therefore, they hopped on a Metro North train and started exploring the towns outside the city. 

Initially, I felt badly that they traveled all the way from Italy and didn’t enjoy the Big Apple, but in typical Italian “go with the flow” form, they didn’t seem the least bit upset about the change in plans.  In fact, when I expressed disappointment that his vacation was taking a different turn, he looked at me, pointed to the nearby houses, and exclaimed, “Your villas are beautiful!”  I laughed, and replied, “Actually we think YOUR villas are beautiful!” It was a helpful reminder that sometimes we take the world around us for granted, and it was refreshing to see my own neighborhood through his eyes. 

Well, a year later, COVID has drastically changed the world of travel, but one silver lining for those of us itching to escape is that we’ve chosen to more thoroughly explore our own “backyards.” On that day in the park, I suggested a few places to visit within 2 hours of NYC. You may not be a lost Italian tourist, but if you’re in NYC or live nearby, and need some new creative exploration ideas, here are some of my favorite weekend escapes from NYC to check out:

Hiking in Ellenville, New York

Fall hike at Sams Point, New York- weekend escapes from NYC
view from Sams point, New York - weekend escapes from NYC

Strap on your hiking boots and the hit the trails in the countryside for a little break from the “Concrete Jungle.” There are countless hiking options within 2 hours of the city, and one of my favorites (especially in the fall) is Sam’s Point.  It’s a relatively easy trail at the beginning, with options to explore other more challenging off-shoot paths. 

Time from city: Approx. 2 hours

COVID precautions: Go here for real time updates and closures due to COVID. 

Compass Roam pro tip: Arrive early as parking is limited. In addition, I accidentally hiked the longer loop, which I didn’t realize was a 6-hour journey.  Next time, I’d hike towards the waterfalls, and then turn back. This website has a trail map to help guide you. No matter which trail you choose, don’t forget to pack a picnic and enjoy the views.


girl viewing beluga whale at mystic aquarium- weekend escapes from NYC

Mystic is a small seaport Connecticut town filled with shops, good food, and kid friendly activities.  You can spend the afternoon poking in and out of cute stores, and enjoying a leisurely lunch at Bravo Bravo. I loved the eggplant “meatballs” and cacio e pepe.  The staff took COVID precautions seriously, and the large restaurant windows allowed for plenty of air circulation.  After lunch, make a stop at the Mystic Aquarium to show the little ones about life under the sea.   I did not spend the night in the town, but loved the inviting and cozy look of The Whaler’s Inn.

Time from city: 2.5 hours

COVID precautions: Advanced reservations required for the aquarium.


map of pizza locations in new haven

When I started dating my husband, I quickly learned that it was going to be a “relationship requirement” to eat (and love) mashed potato pizza.  The first time I heard about this unique combo, I responded with raised eyebrows, and a questionable stare.  I love trying new foods, but this seemed like an odd marriage of flavors.  However, New Haven was my husband’s former stomping ground, and I soon realized that until I tried all the city’s famous pizza joints, I would never truly have his heart. 

For those of you unfamiliar with New Haven, the pizza wars in this city rival that of the famous Philly cheesesteak battles further south — in other words, pizza is serious business. So, off we went to eat at FOUR pizza places in one day. My husband wanted to design a fair day of competition, so we ordered a regular cheese pie at each location (test group), as well one speciality pie (experimental group). At the end, there was a vote.  I won’t bias you with my gold medal choice, but I will say that I now believe mashed potato and pizza are a match made in heaven. Here are the spots you won’t want to miss on your own pizza tour of New Haven:

Time from city: Approx 1.5 hours.

COVID precautions: Call ahead to inquire about outdoor dining, or if necessary to make a reservation.

Compass Roam pro tip: Don’t eat breakfast today.  Start early, pace yourself, don’t overeat at the first location, and only focus on the pizza (no salads or other dishes). 


Photo courtesy of Rebecca Yale Photography
Photo courtesy of Rebecca Yale Photography

Hudson holds a special place in my heart, as it’s where Niall and I got married.  However, if you’re headed here without wedding bells in mind (or maybe future ones), you’ve picked a perfect spot for a weekend away.  We fell in love with this charming town, and have returned a few times to show our daughter “where it all began.” There is an old-town style main street with boutiques, cafes, and no shortage of antique stores! If you’re feeling up for a hike, there are also plenty of trails nearby. Or, if your heart is set on some pie (like mine), you’ll find farm stands along the back roads with fresh ones waiting. I recommend spending the night at Mount Merino Manor, which is a tastefully designed bed and breakfast. It has a large beautiful property, and the best peach pancakes around. Lastly, if you happen to be wedding venue shopping, The Hill was a magical place to say “I Do.”

Time from city: Approx. 2 hours (Metro North) 

COVID precautions: Call ahead to inquire about store hours, and restaurant/hotel restrictions.


entrance to Blue Hill Restaurant at Stone Barns - weekend escapes from NYC
Dining area at Blue Hill at Stone barns - weekend escapes from NYC
peach melba dessert at Blue Hill
Picnic basket display at Blue Hill

If you’re looking for the perfect surprise gift, or an extra special night out, you can’t go wrong with the full foodie experience at Blue Hill at Stone Barns.  The buildings and barns seem like they are right out of a movie, and have an Old European vibe meets New York farm feel.  The chef decides upon the daily menu, with dishes inspired by the produce harvested from the farm and gardens.  In pre-COVID times, it was possible to eat one course of the meal in the kitchen right next to the chefs!  Hopefully this resumes when it’s safe to do so, because it was one of the most unique and memorable culinary experiences I’ve ever had.  It’s pretty exciting to be eating fresh pasta amidst the buzz and commotion of the final plating.  It’s kind of like the foodie-equivalent of sitting courtside at a basketball game.

During COVID, the restaurant adapted the typical dining experience by creatively taking the concept of picnicking to a Michelin star level.  Restaurant go-ers enter into a beautiful courtyard to find their assigned picnic seating, a welcome drink and picnic weave basket containing the night’s tastings.  My summer favorites were the Pimenton Gazpacho, cherry tomato salad with goat cheese, cucumber and grilled watermelon, warm potato salad, and the peach melba. I returned at the end of October for a fall feast including roasted squash, puffed mushrooms, and a blueberry mousse.  Beware, once you’ve had a picnic at Blue Hill, you’ll forever need to elevate your picnicking standards!

Time from city: Approx 1 hour.

COVID precautions: Advance reservations required

Compass Roam pro tip: Dress warmly! Once the sun sets, it gets quite chilly at night.


beach at Tod's point - weekend escapes from NYC
sunset at Tod's point

If you’ve never taken an adventure to Greenwich on Metro North, it’s an easy and fast train ride from the city, and the station is within walking distance from “The Ave.”  Greenwich Ave has name brand stores, like Lilly Pulitizer, Athleta, and Apple, but also boutique shops that are unique to the town. 

If shopping isn’t on your “escape from the city” activity list, there are plenty of outdoor exploration options.  Check out Mianus River Park for easy walking trails.  Alternatively, head to Tod’s Point (Greenwich Point Park) for views of the Long Island Sound and the NYC skyline.  There is beach access, and walking trails throughout the preserve.  It’s fun to go hermit-crab hunting with the little ones during low tide, and don’t forget to pack a picnic dinner for the spectacular sunset. 

Time from city: Approx 45 min-1 hour

COVID precautions: Some snack stands and restrooms may have limited service.

Compass Roam pro tip: Note, a town pass is required to access Tod’s Point from April-October, but the park remains open to anyone during the off-peak season.  If you’re in town during the warmer months, you can obtain a park pass from the town hall.  Find the info for obtaining a single entry pass here. Note: To access Tod’s Point or Mianus, you will need your own car (there’s no train access).

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