Best Day & Weekend Trips From NYC



We New Yorkers have been cooped up for way too long, and it’s about time we saw the light of day, experienced some nature outside of our lonely house plants, and stimulated our senses with everything the outside world has to offer.


Here’s a guide for all my adventurer’s out there: the small-town dreamer, the glamper, the lake-side bird watcher, and the outdoorsman (and woman).


Charming small-town getaways


Saratoga Springs, NY

Probably most famous for the Saratoga Race Course, which features horse racing from July to September, Saratoga Springs offers many, many highlights. This year, it even made TravelMag’s list of top 30 charming towns in the country, offering countless shops and boutiques, cafes and restaurants, entertainment venues and nightlife, and plenty of historic sites for the American history buffs out there.


Woodstock, NY

Ah, Woodstock – probably exactly what you need after too much time spent in the crowded city. The town has become known over the years as a sort of utopian art colony, so there are many art galleries to visit and even workshops to participate in at the Woodstock Byrdcliffe Guild. Woodstock’s famous Tinker Street is filled with quaint cafes, bookstores, outdoor markets, musicians and performers, and constant bustling activity. If you’re into the music scene, make sure to check out the Bearsville Theater, which hosts weekly indie performers, and Village Green.


Glamorous getaways


Oheka Castle - Huntington, LI

You don’t have to go far to get lost in the magic of a historic castle with grounds that stretch for acres and take your breath away. Oheka Castle is one of the Gatsby Gold Coast Mansions, and is actually the location where Gatsby imagined his most well-known book, The Great Gatsby. Oheka is the perfect combination of French elegance and American history, and you can explore all of that in the mansion itself (there are tours), its many gardens, and its indoor and outdoor restaurants.


Glenmere Mansion - Chester, NY

Glenmere Mansion is a world in itself that immerses you in luxury, tranquility, and a true physical and mental getaway. Surrounded by 150 acres, Glenmere sits at the top of a hill and provides its guests with the royal treatment: beautiful guest accommodations, two restaurants, recreational facilities, spa treatments, countless meadows and gardens, what more could you ask for? The area outside of the mansion is also sprinkled with vineyards, a race track, and the rest of Chester and the historic Hudson Valley.


Beach & Lake-side getaways


Montauk, NY

Montauk kind of falls under each one of these categories, offering a little of everything: a vacation by the water, a luxurious spa weekend, a visit to state parks, and a charming small-town retreat. Ideally, you’ll do all of these things while you’re there, but your options are all available to you. A perfect day would consist of an early morning walk on the beach, some breakfast in town (take your pick), a hike up to the lighthouse, and a fire-pit dinner at Gurney’s.


Lake George, NY

Summer is the perfect time to get to Lake George; all you need is a bathing suit, some cold drinks, and an out-of-office message. The plan here is to head out to the water early, get a little sunkissed, eat lunch at one of the many outdoors restaurants this place has to offer, shower and rest up at a lakeside resort (these range from reasonable to four-dollar-signs), and have dinner at yet another of the many outdoor restaurants. If you’re looking for a side of history with your beach vacation, the Fort William Henry Resort is the place to be.


Culture getaways


Rhinebeck, NY

Rhinebeck is one of the most interesting historic towns along the Hudson River - home to less than 10,000 residents, this town has managed to keep its historic charm perfectly intact. With a farm-to-table movement, there’s plenty of selection for delicious restaurant visits as well as a bustling arts and boutiques scene. Aside from all of the museums to visit, there are also more authentic historic homes and architecture everywhere you turn. To get the most of this place, book your stay at the Beekman Arms Inn, America’s oldest!


Sleepy Hollow, NY

Sleepy Hollow is probably one of the most famous colonial-era towns in New York, and if you haven’t heard of it, it’s about time you did. The town set the scene for Washington Irving’s The Legend of Sleepy Hollow, and it’s known for its renowned Halloween festivities throughout the month of October. Rest assured, there’s plenty to do during the rest of the months too: visit seventeenth century churches, listen to some sunset jazz, check out historic sites (ahem, Sleepy Hollow Cemetery), visit tons of farmers markets, and more.


Hiking getaways


Hudson Highlands State Park

Hudson Highland’s is the center point for many different hiking trails, all of which can be found on All Trails, but a popular favorite is Breakneck Ridge. The 3-mile trail is true to its name, with parts of the way steep enough to just call it rock climbing, so you might want to leave the kids at home for this one. There is an abridged version of the hike for those of you who want the beautiful scenery without the super elevated heart rate, but the reward for completing the more difficult trail is a view of the Hudson and all its surroundings from the very top.


Harriman State Park

Another popular spot for day-hikes is Pine Meadow Lake in Harriman State Park. There are two options here as well, one 5-mile hike that ends at the lake, and one 10-mile hike that continues around the entire thing. Either way, the trail offers several peaceful hours of nature and a calm lake - a perfect break from our ever-busy city.


Go forth and explore!