For the 50+ Traveler

A road trip from New York City to Boston is on many bucket lists. Most people drive the coastal route with stops in Connecticut and Rhode Island. As an alternative, try going inland through New York State and Western Massachusetts. You will discover many cultural, culinary, and historical hidden gems on this road trip.

This road trip can be done any time of year. On an autumn trip, you will see amazing fall colors. Spring brings an abundance of flowers. It is doable in winter, but some spots are seasonal and the roads can get snowy. Summer is full of interesting events and a lot of crowds.

The skyline of New York City.

Start Your Trip In New York City

New York City is a fantastic destination any time of year. Culture, theater, food, parks, and history -- it’s all there. If you are a first-time visitor, you may want to focus on the top attractions: Central Park, the Statue of Liberty, the Empire State Building, the Brooklyn Bridge, Grand Central Station, Chinatown, and Broadway.

As a native New Yorker, I like the hidden gems of New York, and you might also include a trip to Brooklyn, Queens, Staten Island, or the Bronx as part of your adventure.

New York is one of the culinary capitals of the world, so be sure to sample the many ethnic cuisines in the city. Chinatown, Curry Row, Katz’s, and Yonah Schimmel Knish Bakery are definitely worth a try.

Once you’ve had your fill of the Big Apple, it’s time to get on the road. First stop: the Hudson Valley.

A bridge over the Hudson River in Hudson Valley.

Spend A Night In The Hudson Valley

The Hudson Valley begins just north of New York City and extends all the way to Albany. On this road trip, you’ll be going through the lower part of the Hudson Valley, about an hour’s drive from Manhattan.

The Union Church of Pocantico Hills in New York.

1. See Stained Glass Masterpieces

The first stop is a hidden gem. Built by the Rockefeller family, the Union Church of Pocantico Hills is a small, unassuming church with nine stained glass windows by Marc Chagall and one by Henri Matisse. Take a moment of quiet reflection and to admire the stained glass. Photography is not allowed inside the church. It is wheelchair accessible and a short walk from the parking lot.

Kykuit, the Rockefeller Estate in New York.

2. Visit Kykuit, The Rockefeller Estate

The Hudson Valley is full of historic sites that date to the gilded age, including the Rockefeller and Vanderbilt estates as well as those of Presidents Martin Van Buren and Franklin Roosevelt. Pick at least one to visit.

Our favorite is Kykuit, the home of four generations of Rockefellers. The gardens, views, and homes are spectacular. You can only visit Kykuit by booking a tour. It is best to buy your tickets in advance, especially if you are visiting in the summer. The art galleries are included on the three-hour tour.

The grounds are extensive, so walking shoes are important. Some parts are accessible, but not all. When booking a tour, check the website for full accessibility information.

For a dinnertime splurge, Blue Hill at Stone Barns is nearby. This farm-to-table restaurant is amazing but very expensive. There are many affordable restaurants, hotels, and bed-and-breakfasts in Tarrytown and the surrounding areas, too.

If you are in the Hudson Valley during October, Sleepy Hollow is a great place to experience Halloween for children and families.

After checking out of your overnight stay the next morning, head up to New Windsor, about an hour’s drive.

The sculpture garden at Storm King Art Center.

3. See The Outdoor Sculpture Garden At Storm King Art Center

Storm King is a 500-acre outdoor museum with large-scale sculptures. It is stunning any time of year. Our favorite time to visit is in autumn when it is less crowded and the fall colors light up the area. Sunscreen, insect repellent, and good walking shoes are in order. If you have mobility challenges, a tram traverses the grounds and is equipped for wheelchairs.

For lunch, there is food onsite and in nearby restaurants. Alternatively, take a 40-minute drive to our next recommended stop: the Culinary Institute of America.

The Culinary Institute of America in New Hyde Park.

4. Culinary Institute Of America

Want to see where the next top chef is being trained? Stop by the Culinary Institute of America (CIA). CIA was the first college to offer culinary arts instruction in the U.S. The late celebrity chef and host of Kitchen Confidential, Anthony Bourdain, was an alumni.

Located in beautiful New Hyde Park, the CIA primary campus is a good place to visit for an hour. The school has a cafe and two restaurants on the premises. Reservations are recommended and are sometimes booked up months in advance.

The Old Rhinebeck Inn in New York.

5. Spend The Afternoon Antiquing In Rhinebeck

Rhinebeck is a short 20-minute drive from CIA. It is very popular for antiques. You can find treasures anytime of the year, and there is a huge antique show in October. If you visit in July, there is a hot air balloon festival. In May, you’ll find an antique car show.

Stay overnight in Rhinebeck. Make sure to book your room in advance if you are attending one of the festivals. The Old Rhinebeck Inn and the Fiddlers Farmhouse are two possibilities.

The Massachusetts Museum of Contemporary Art.

6. Cross The Border Into Massachusetts And Visit MASS MoCA

Get on the road first thing the next morning for the two-hour drive to North Adams, the home of the Massachusetts Museum of Contemporary Art (MASS MoCA).

Located in North Adams, MASS MoCA is one of the largest contemporary art and performing spaces in the country. Housed in a converted print factory complex, the museum is known for its oversized modern and contemporary installations not usually found in traditional galleries. In addition to special exhibitions, MASS MoCA offers a wide variety of music, sculpture, dance, film, painting, photography, and theater. The museum has an excellent bistro on site.

The place to stay when visiting MASS MoCA is across the Hoosic River. The Porches Inn is a charming boutique inn converted from a row of beautifully restored 19th-century Victorian homes. Named for its porches filled with rocking chairs, it is very cozy with working fireplaces and claw-foot tubs. The inn blends whimsical comfort with modern amenities.

The Botanic Garden of Smith College in Northampton.

7. Spend A Day In Northampton

An hour’s drive from MASS MoCA, Northampton and nearby Amherst are college towns. Smith, Hampshire, Amherst, and Mount Holyoke Colleges are located there. The Botanic Garden of Smith College is worth the trip. You can also wander Main Street to see the art galleries. Want to travel off the beaten track? Visit the Yiddish Book Center in Amherst. The center is dedicated to the preservation of Yiddish, the language of eastern European Jewish communities. More than a million books are collected there.

It’s a two-hour drive to the next stop -- Salem, famous for the Salem witch trials of the 1690s.

The Salem Witch Museum in Salem, Massachusetts.

8. Experience All Of Salem

Salem has much to offer and could easily be an overnight stop or a day trip from Boston.

Of the many tourist attractions related to the Salem witch trials, our favorite is the Salem Witch Memorial to the 20 men and women who were tried and executed. Fans of Nathaniel Hawthorne can also take a walk to see the House of the Seven Gables, the setting for the novel.

The Peabody Essex Museum is also a must-see. Its collection spans widely from maritime artifacts to Asian and African art.

While in Salem, make sure to go to the Punto Urban Art Museum on the other side of town. The area has extensive murals painted by local and internationally famous artists. It is part of an effort by the North Shore Community Development Corporation to use street art as a social justice and community development effort.

Once you are done in Salem, make the 40-minute drive to Boston where you will spend the next three days exploring the city.

The skyline of Boston, Massachusetts.

9. Learn About American History In Boston

You’ve now arrived in Boston, a city with many historical gems. Some favorites are the Freedom Trail, Paul Revere’s house, and Faneuil Hall. Perhaps you’ll want to catch a baseball game in Fenway Park, soak in the sun in Boston Commons, or grab a drink at the famous Cheers bar. Crossing the Charles River will bring you to Harvard , MIT, and Cambridge.

Pro Tips

Take your time to savor the scenic drives on this road trip and the hidden gems throughout the Hudson Valley. If you enjoy bed and breakfasts, there are many. Make sure to book your accommodations well in advance if you are traveling in the summer or during one of the many festivals. If you want to dine at the Culinary Institute of America or Blue Hill at Stone Barns, we recommend making reservations months in advance.