5 Weekend Trips and Getaways From New York City

Spend the weekend in Gloucester, a postcard New England coastal town
Spend the weekend in Gloucester, a postcard New England coastal town | © Hemis / Alamy Stock Photo
Photo of Molly Codyre
1 April 2021

Life in the concrete jungle can be exhilarating, but sometimes you need a change of pace. Luckily for residents of the Big Apple, there are a number of spots within striking distance that you can head to for a weekend breather. Whether you want a healthy dose of salty coastal air, or prefer to delve into the country’s darker history, you’ll find something to suit your needs. Replace sky-high buildings with towering trees on any of these weekend trips and getaways from New York City.

Portland, Maine

Not to be confused with the hip Oregon city, Maine’s Portland has long been the poster child for the quintessential Northeastern port town. But while fishermen still operate here en masse, the city is seeing something of a cultural revival. An influx of trendy new restaurants has revived the dining scene, and the coastal city is blossoming into a buzzing cultural hub that attracts visitors from all over. Quaint, but with just enough up-and-coming spots to keep you busy (and score you some I-was-there-first points), it’s the perfect weekend break.

Experiences curated for you

Special days out

We check thousands to find special and memorable experiences.

Whatever your budget

From parks, museums to expert classes, there is something for you.

Stress-free booking

Secure booking, customer support and cancellation options.

ToursPortland: Old Port Culinary Walking Tour
From $129 per person
2 to 3 hours
4.9 (11)
You can explore the Old Port independently, but to uncover the best places serving traditional local fare, this guided tour is your best bet. Taste the best that Portland has to offer at up to seven different stops – enough tastings to replace a meal. Along the way, your guide will tell some stories about Portland’s food scene, so you can discover the city’s culinary history and get familiar with its local stalwarts.

Salem, Massachusetts

If you were ever a fan of Sabrina the Teenage Witch, or simply have an affinity for the occult, Salem is the destination for you. There are, of course, activities in town that don’t relate to its “witchy” past – such as feasting seaside on fresh lobster – but the best way to enjoy a trip here is to throw yourself into its infamous history. The most atmospheric time to visit is October, when the whole month is dedicated to the city’s Haunted Happenings festival.

Tours1692 Witch Trials Walking Tour in Salem
From $15 per person
1 hour 30 minutes
4.2 (28)

This walking tour is the best way to gain insight into the infamous 1692 witch trials that turned neighbor against neighbor. Skipping over the elaborations of the stories, and instead depicting the factual events as they happened, this tour shines a light on an often misunderstood period of Salem’s history. Visit pivotal sites such as the witchcraft memorial and courthouse, and gain a better understanding of this fraught historical event through the stories of the accusers and victims.

Gloucester, Massachusetts

Named by its English founders in 1623, Gloucester is a postcard New England fishing town. The oldest seaport in the country, its 400-year history of angling is memorialized with a statue on the waterfront, and while the town has been modernized in recent years, it has stayed true to its watery roots. Spend your weekend exploring the rugged seaside and devouring fresh-off-the-boat seafood by the water.

Newport, Rhode Island

Home to sprawling mansions and a dining scene that encourages dinner jackets, a stay in Newport is an opportunity to experience how the other half live. Games of tennis (in immaculate tennis whites, of course), strolls along the waterfront and tours of Gilded Age mansions are the order of the day here, where weekends away feel like a chapter out of The Great Gatsby. It’s glamorous and restful in equal measure.

ToursNewport Walking Food Tour
From $75 per person
150 to 180 minutes
4.8 (8)

Dabble in the town’s dining scene and immerse yourself in its glittering history on this walking tour, which will feed you as much with food as it does notable facts. Making you way around five restaurants, you will also visit notable local spots such as The Elms Mansion, built in 1901, and Samuel Whitehorne House, built in 1811. Your guide will take you through the history of the town, from before the American Revolution, through the Gilded Age, and up to the present day, allowing you a much more in-depth understanding of your temporary weekend home.

Bird-in-Hand, Pennsylvania

Named after the saying “a bird in the hand is worth two in the bush,” which refers to the idea that it is better to have a small certain advantage than the possibility of a greater one, Bird-in-Hand was founded in 1734 in Lancaster County. It remained relatively unknown until the musical Plain and Fancy opened in New York City in 1955 with the town as its setting (but thanks to its success, there is now a restaurant in the town named after the play). Set in the heart of Amish country, the town is a testament to Amish hospitality and offers a true respite from city life.

ToursAmish Experience Visit-In-Person Tour
From $60 per person
3 hours
5 (2)
Step off the typical tourist trail and venture to a working Amish farm, where you’ll see how cows are milked and discover fascinating aspects of farm life, including how milk is kept cold with “Amish electricity.” Then, visit the studio of an Amish craftsman, where they make everything from gazebos to quilts. Finally, drop by an Amish family home, where you can relax and converse with members of the local community without the distractions of modern life. This is an insightful experience that welcomes you into an often misunderstood community.

Cookies Policy

We and our partners use cookies to better understand your needs, improve performance and provide you with personalised content and advertisements. To allow us to provide a better and more tailored experience please click "OK"