Edited 3/10/23
This summer I have been taking a lot of weekend road trips from NYC. This has been the perfect way to escape the crowds of the city while also exploring some of the beauty just outside of the big apple. While I miss traveling internationally, I have enjoyed the opportunity to explore some areas close to home that I previously never had the chance to visit. Below I have outlined the details of a few of my favorite weekend road trips from NYC, including driving length and recommendations of things to do in each place.
All of these locations make excellent weekend road trips from NYC and have many outdoor activities that are perfect for having fun while social distancing. Remember to be considerate of the places that you are visiting and follow local guidelines for Covid-19 safety. Make sure to always keep a spare mask with you as well as carry plenty of hand sanitizer!
I have organized the destinations by distance, starting with the places that are closest to NYC and can easily be visited in just one day, and ending with the places that are further away from NYC and would require a night or two at a local accommodation.
Below are ten of my favorite weekend road trips from NYC!
1. Hudson Valley and The Catskills
- Distance from midtown:
- By car: 45 minutes-2.5 hours
- By train: 1-4 hours
The Hudson Valley is located directly north of NYC, stretching from Westchester County up to Albany. A few of my favorite towns in the Hudson Valley include Nyack, Cold Spring, and New Paltz. There are many hiking options in the area. I would recommend using this site (https://www.alltrails.com/explore/us/new-york/new-york-city) to find a hiking trail that is the right length and difficulty level for you.
In addition to hiking, a few of my favorite experiences in the area include kayaking the Hudson River in the town of Cold Spring (this is one of many fun things to do in Cold Spring), getting brunch and exploring the grounds at the Mohonk Mountain House, and taking in the beautiful views at Benmarl Winery.
2. Jersey Shore
- Distance from midtown:
- By car: 1 hour
- By train: 2 hours
I used to think of fake tans, fist pumping, and parties whenever I heard the phrase “Jersey Shore”. However, the majority of the New Jersey Shore isn’t anything like the show on MTV. The Jersey Shore has over 100 miles of beautiful sandy beaches and a variety of towns and boardwalks to visit. Most beaches along the Jersey Shore require a beach pass which can be obtained using the app “Viply”. Some of the more popular beaches such as Asbury Park and Avon by the Sea sell out of daily passes pretty quickly. Daily passes go on sale in the evening for the following day, so I would recommend purchasing your passes the evening before you plan on visiting. I visited “Seven Presidents Beach” and was really impressed by the huge shore line and lack of crowds, making it an easy place to enjoy the beach while social distancing. This is one of the closest beaches outside of the five boroughs, making it an easy weekend road trip from NYC.
3. North Fork, Long Island
- Distance from Midtown:
- By car: 1.5-2.5 hours
- By train: 2.5-3.5 hours
I love visiting the North Fork of Long Island for it’s amazing wineries, farms, and food.
A few of my favorite vineyards include Sparkling Pointe (they have fantastic sparkling wine made using the champagne method), Pindar Vineyards (I love their Summer Blush Rosé), and Martha Clara Vineyards. If you are not a huge wine person, you could also visit The Riverhead Ciderhouse, Twin Stills Moonshine, or Greenport Brewery.
In addition to wine tasting, some other fun activities include berry, apple and pumpkin picking, visiting the lavender fields, and strolling around the town of Greenport. My favorite restaurants on the North Fork are Farm Country Kitchen and Lucharitos. Be sure to also stop by Briarmere Farm for its famous homemade pies and pastries.
Looking for more info? Check out my blog post “15 Best Things To Do On The North Fork“
4. Montauk/The Hamptons
- Distance from midtown:
- By car: 1.5-2.5 hours
- By train: 2.5-3.5 hours
Montauk and The Hamptons are located on the south shore of eastern Long Island. There are a variety of towns you can visit, starting with the Westhampton, Quogue and Hampton Bays area. This area has a laid back vibe, beautiful beaches, and some great waterfront restaurants such as @rumba_hamptonbays , @cowfishhamptonbays , and @oaklandsrestaurant .
Next are the towns of Southampton, Bridgehampton and East Hampton which is the core of “The Hamptons”. This is the most expensive area to visit and you are very likely to spot celebrities there. If you visit this area be sure to grab a bagel at Goldbergs and cookies at Le Vain bakery. If you are looking to splurge, you can also treat yourself to a nice outdoor dinner at the 1770 House Restaurant.
Just past “The Hamptons” is the town of Montauk which is the easternmost point of Long Island (and New York State). It is less fancy than the nearby Hamptons towns, having more of a surf and fisherman vibe. I recommend checking out the incredible views at the lighthouse, and then grabbing a beer at the Montauk Brewery (their summer Watermelon Ale is my favorite!). You can get to Montauk by taking the LIRR, the Hampton Jitney, driving, or by private helicopter (kind of kidding on that last one… unless any of you guys do plan on chartering a helicopter please invite me along 😜)
5. Poconos
- Distance from midtown:
- By car: 2 hours
- By train: not recommended
The Poconos are a great option for an affordable weekend road trip near NYC. I usually visit the Poconos in the winter for skiing, but it is also a popular summer destination. Summer activities include kayaking in the Delaware River, hiking Bushkill Falls (known as the “Niagara of Pennsylvania”), and boating or jet skiing in one of the area’s many lakes. Airbnb’s and hotels in the Poconos tend to be pretty affordable, making it a great weekend road trip from NYC if you are on a budget.
6. Newport, Rhode Island
- Distance from midtown:
- By car: 3 hours
- By train: 5+ hours (not recommended)
Newport is famous for it’s sailing, historic mansions, and goat farms 🐐 .
Okay, maybe Newport is not famous for it’s goat farms, but they DO have some adorable goat farms where you can feed and play with the goats! In addition to goat farms, Newport has a cute downtown area filled with restaurants, fudge/ice cream shops, and clothing boutiques. If you take a weekend road trip from NYC to Newport I would recommend staying for at least a night or two since it can be a long drive to get there, especially if you hit traffic.
7. Pittsfield, MA
- Distance from midtown:
- By car: 3-3.5 hours
- By bus: 4 hours (limited service, not recommended)
This winter I visited Pittsfield, MA for the first time and was blown away by the amount of things to do in the area.
Located in the heart of the Berkshires, Pittsfield is a great destination to visit anytime of year. In the winter you can enjoy skiing, snow boarding, and snow tubing, in the spring you can go hiking in their many nearby trails and parks, in the summer you can enjoy water sports such as boating and kayaking, and in the fall you can take in views of the changing leaves.
My favorite thing about Pittsfield is that in addition to having an abundance of nature activities, there is also a great downtown area with fantastic restaurants, bars and breweries. There is also a huge arts scene with multiple theaters offering weekly performances year-round. Check out this post for more info about visiting Pittsfield!
8. Cape Cod
- Distance from midtown:
- By car: 3.5-5 hours
- By train: Not recommended
- By ferry: There is a high speed ferry available from NYC to Nantucket, but it is very expensive!
This summer I spent a week in Cape Cod and was blown away by the amount of fun things to do in the area! I did not know much about Cape Cod before visiting, so here is a quick breakdown of this popular vacation spot:
- Cape Cod is a hook shaped peninsula located 70 miles south of Boston.
- It is very big! It takes about 90 minutes to drive from the “Upper Cape” furthest inland to the “Outer Cape” at the tip of the peninsula.
- Cape Cod has a huge shoreline, including bay-side beaches facing Cape Cod Bay, and ocean beaches facing the Atlantic. I enjoyed both equally!
- The nearby islands of Martha’s Vineyard and Nantucket are technically not part of Cape Cod, but are easily accessible by ferry.
Check out my blog post for a complete list of fun things to do in Cape Cod.
If you are visiting Massachusetts in the fall, be sure to also visit the town of Salem which is located about one hour north of Boston. It is the perfect destination for Halloween lovers! Here are some of the top things to do in Salem, MA.
9. Fingerlakes, NY
- Distance from midtown:
- By car: 4-5 hours
- By train: not recommended
The Fingerlakes Region is a group of 11 lakes located just north of Ithaca. This area is a famous wine producing region well known for its Riesling and Gewurztraminer. In addition to wineries, there are many state parks with trails for hiking and biking, and campsites available. There are also a number of waterfalls in the area.
Check out my blog posts about the Best Wineries in the Finger Lakes and the most beautiful Waterfalls in the Finger Lakes
10. Baltimore, Maryland
- Distance from midtown:
- By car: 3-4 hours
- By train: 3 hours
Baltimore is a great city for a weekend trip. There are a ton of fun activities in the city, such as exploring their neighborhood of Fell’s Point, going brewery hopping, and taking the Baltimore Water Taxi. For more activity ideas, check out this itinerary for a Baltimore Weekend Trip.
Have you visited any of the above destinations? Which one was your favorite? Leave a comment below!
