The Best Winter Vacation Road Trips Ideas From the Big Apple

Winter Vacation Road Trips Black car

There’s never an “off” season in a city like New York, but the holiday season can be especially bustling. The crowd-drawing activities like the Rockefeller Center Christmas tree lighting. The increase in shopping in Manhattan is a pretty chaotic place to be during the winter. If you’re visiting this winter or you have loved ones coming, take advantage of our New York car rental specials. Then do yourselves a favor and plan a little escape.

You don’t have to go far from the city to find serenity and different scenery. New York is a very large state, and it’s filled with places and activities for every taste and budget. If you’ll be around for a week or longer, you owe it to yourself to take one of these short adventures and see some new sights.


Hudson, New York

Looking for most of the amenities of a big city packed into a small town? You’ll love Hudson, which is a 120 mile drive from the heart of Manhattan. The city itself is very walkable, so you can park your New York luxury car rental as soon as you arrive and walk around on foot. You’ll discover an amazing antiques market along with historic streets and buildings, salons, art galleries, vintage clothing, three museums and some delicious restaurants. Spend the night in one of the 10 Bed and Breakfasts so you can head back into the city feeling rested and rejuvenated.

Highland Falls, New York

The village of Highland Falls is located in the town of Highlands, which is about 50 miles north of New York City. Main Street comes to a halt at the United States Military Academy at West Point, making it a popular tourist destination. Don’t miss the Cadet Chapel, a Gothic church built in 1910, or an academy tour. Four miles downriver you’ll see some Revolutionary War history at Fort Montgomery. It’s open every day, but the Visitors’ Center is closed Mondays and Tuesdays.

Greenwich, Connecticut

Greenwich is a mere 39 miles from New York, but allow yourself an hour and a half to make the drive. This charming town on the river is home to a lot of people who work in the city but prefer to come home to a more suburban dwelling. If you’re planning a weekend getaway here, don’t pass up an opportunity to either dine or stay at the Homestead Inn. This timeless boutique hotel offers luxurious accommodations and beautiful scenery. Tourist attractions include the Bruce Museum and the Philip Johnson Glass House, among others.

Newport, Rhode Island

If you have a few days to spare, make the 180 mile drive from the city to Newport, Rhode Island. The beaches and seafood are top notch, and winter is a slower time for tourism. The Newport Tour & Guide company offers private guided tours year-round. Winter is the best time to take advantage of their specials. Make sure you try a lobster roll (or two) before you head back into the city. If you time it right, you can also enjoy the Newport Winter Festival in February and celebrate with the locals.

Oyster Bay on Long Island’s North Shore, New York

There’s a reason Billy Joel once sang “I wish that I was back in Oyster Bay, takin’ it easy…” Oyster Bay is a charming place, and the area around it is perfect for exploration. Along with obvious abundance of delicious oysters and seafood. Visitors can enjoy historical sites such as the Theodore Roosevelt Sanctuary & Audubon Center and the Sagamore Hill National Historic Site. This is one getaway that will have you back in the city by bedtime.

Lake Placid, New York

If you’re into snow sports or just love a good winter landscape, make Lake Placid your destination of choice. Allow yourself a few days for this one—Lake Placid is a good 290 miles away from New York City. But this is where you’ll want to be to enjoy some of the country’s oldest natural attractions, including High Falls Gorge and Ausable Chasm. One of the top family attractions is Santa’s Workshop, which has been delighting children and kids at heart since 1949. If you’ll be around for the holidays, take a trip back in time to this storybook village.