Fall Foliage Drive (Weekend Escape from NYC)

It's always been on my bucket list to go on the quintessential New England fall foliage drive, and what better time than now to escape the city for a weekend with nature? For those of you lucky enough to get away for an entire week or more, I envy your time to explore all of New England! One of these autumns, I plan to do the full tour up through Vermont and into Maine to fully soak in the beauty of fall (and beyond - I've had so many friends visit Maine this summer!).


For those who only have the weekend to explore consider, following the very scenic route I took through Connecticut and Massachusetts, with some very some fun stops along the way. It was beautiful, colorful, and most of all relaxing -- something we can all appreciate these days.



Renting a car in NYC

Unless you're lucky enough to own a car in the city or have access to one for free from a family member or friend, you're going to have to rely on a rental. Unfortunately, rentals will come at a premium in NYC, so be prepared to pay over $100-$200/day coming with pick-up/drop-offs in Manhattan from any major rental company (Avis, Hertz, National, Budget, etc.). While it may be worth it for some for the convenience, I would look into picking up your car from a different city or out of state if possible. I guarantee it will be much cheaper and may even shave off some time from your drive and you get to by pass the heavy traffic out of the city anyway.


We chose to take the Metro North from Grand Central to Stamford, CT., where we picked up our car from Avis right outside the station. We saved ourselves the headache of sitting through Friday night rush hour traffic, AND saved ourselves a couple hundred dollars simply by picking up the car outside of NYC. Our total came out to be ~$125 for Friday-Sunday night, even with drop-off back in NYC.


After picking up the car in Stamford we drove North about an hour to Danbury, CT to continue our drive bright and early on Saturday morning.


Day 1: Saturday

Danbury, CT -- Macedonia State Park, CT -- Great Barrington, MA


Blue Jay Orchards

The first stop on the official foliage tour was a fuel-up at Blue Jay Orchards. During the peak autumn months, you can pick your own pumpkins and apples, which is always a fun activity for all ages. The best part of course is the market, where you can stock up on all the fresh pies, apple cider donuts, local jams, and fresh apples and cider your heart desires.


Macedonia State Park

Located in the charming city of Kent, CT, Macedonia State Park is a beautiful place for a crisp morning hike. If you have a half day, consider taking the 6.8 mile Macedonia Brook Loop. If you're looking for something a bit shorter, the 2.2 mile Cobble Mountain trail will do the trick.


Great Barrington

Great Barrington is one of the most charming towns in the Berkshire region, so make it a point to stop by or spend a half day exploring all it has to offer. There are over 7,200 acres of state forests and hundreds of accessible hiking trails available to create your own adventure. We stopped by GB for a late lunch at Aegean Breeze, a traditional Greek restaurant in the heart of town. I would highly recommend checking it out for a hearty, delicious lunch or dinner.


Where to stay

Peak foliage season in the fall is one of the most popular times in New England for tourists and visitors (even amidst the pandemic). Many Airbnbs, hotels and B&Bs sell out during this time, especially in the Berkshires region, so plan accordingly and book your accommodation well in advance. However, there is also also an advantage to booking your accommodation day-of, so you can decide how far along your drive you want to stop without a pre-planned destination. I'd recommend the first option, but hey, life is also fun when its spontaneous!


Day 2: Sunday

Pittsfield, MA -- Mt Greylock State Reservation, MA -- Mohawk Trail (North Adams to Greenfield), MA -- NYC


Mount Greylock - Stoney Ledge

It isn't hard to come by incredible foliage in New England, especially when you come during the peak of the season. However, we found that some pockets of the drive were definitely brighter and more spectacular than others. Mount Greylock State Reservation is a must for both driving through and hiking. I highly recommend taking Rockwell Road through the park, as this beautiful, winding road is postcard worth from every angle. If you plan on doing a hike (which you definitely should), consider heading up to Stony Ledge from Sperry Road for some stunning, colorful views.


Mohawk Trail

The Mohawk Trail is a 69-mile scenic byway that meanders through historic towns and lush forests. There are actually many different paths you can take within the Mohawk Trail region, so if you have the time to do it, I would suggest picking a few to follow to truly enjoy all that the Berkshires have to offer. We took the Mohawk Trail from North Adams to Greenfield, which was a beautiful 1 hour drive through winding roads and colorful trees lining the trail for 37 miles. I wish we could've taken this scenic route all the way home!


Berkshire Scenic Train Ride in Adam, MA

What better way to experience the fall foliage than on a scenic train ride through the Hoosac Valley? Book your tickets for this 1 hour, 10 mile round trip train ride, voted in the Top 10 foliage train rides in New England! Due to COVID, tickets are only available for purchase in advance, so make sure you do this because it will most likely sell out day-of.

Unfortunately, I did not follow my own advice and we could not book this in time since it was so popular, but it looks like an absolute must-do if you're in the area.

All trains depart from Adams Station in Adam, MA. Keep in mind that train Ride tickets are available for weekend trips on Saturdays and Sundays only, with an exception for Labor Day, Columbus Day, and Black Friday when trips are also scheduled. 


Check out the schedule here for more information.

Photo: Courtesy of Google

Lyman Orchard

I threw this one in here because I just couldn't end the trip without another apple cider to cap off the weekend. Located in Middlefield, CT, Lyman Orchard is a wondering destination for fall festivities. Between the golf club, corn maze, pick your own options and large farmers market, there is plenty to do and eat here for your and the entire family. Unfortunately, I don't have any pictures because I was too excited, but let me tell you - it was a fall vibe.


And there you have it folks - a short, but sweet and colorful weekend away from city. Whether you decide to book a rental for this weekend or bookmark this for next year, I hope this post inspires you to take a well-deserved trip out of town and to enjoy something as simple as the leaves changing color each fleeting fall.

  • Grey Instagram Icon
  • Grey Blogger Icon
  • Grey Facebook Icon
  • Grey Pinterest Icon

© 2020 Penny & Dash by Jessica Ma |