A Perfect Fall Weekend in the Berkshires
The Berkshires are a beautiful area of Massachusetts located about a 3 hour drive outside of NYC and a 2 hour drive from Boston. The Berkshires are famously popular in the fall for the beautiful fall colors and idealistic small town charm. This is the perfect east coast weekend trip to enjoy leaf peeping, beautiful hikes, small town shopping, restaurants, and more!
Getting to the Berkshires:
We drove from Manhattan and really the only way to get there is with a car. You can get close on bus or train, but you’ll still need a car to get around and explore. If you’re flying from out of state, your best bet would be to fly in to Albany (ALB), Bradley (BDL), or Boston Logan (BOS).
Geography:
“The Berkshires” generally refers to Berkshire county which is primarily consists of the cities of Pittsfield, Lenox, Great Barrington, Stockbridge, and Williamstown. We stayed in Lenox and drove around other areas from there.
Day One
Arriving in The Berkshires:
We drove up on a Friday afternoon for our weekend in the Berkshires. We started our drive early and then stopped for our workday at a cute coffee shop in West Stockbridge. No. Six Depot Roastery & Cafe had delicious coffee, lots of tables, and a big space with fast wifi for working, so we spent a few hours here.
Then we made our way to our hotel. We stayed at Life House, Berkshires, a restored roadside lodge that now has the coolest vibes and style.
The rooms are swanky and comfortable, but my favorite part of the hotel is definitely the lobby/library/bar. We spent hours in here because it was so aesthetically pleasing plus the drinks at the bar were great!
Grab a bite:
We sat by the outdoor fire pits at our hotel and enjoyed our happy hour drinks before heading out to dinner. We booked Alta Wine Bar in downtown Lenox and it did not disappoint! They had delicious food with plenty of gluten free options and wine pairings. Then we walked around the charming downtown area of Lenox before calling it a night.
Day Two
Fuel up for the day:
We had a slow morning and then headed to Haven Cafe and Bakery for brunch. This was a popular spot where you order at the counter and then take a seat. Everything was delicious and it was a perfect way to fuel up for a day of exploring.
Lace up your hiking boots:
After exploring the museum, it’s time for some hiking! There are a bunch of options for beautiful fall colors.
- Natural Bridges State Park – the only natural white marble arch in North America
- Ashuwillticook Rail Trail – good for if you want a flat paved trail
If you skipped the museum (because these are in the opposite direction) or are willing to drive a little more, you can check out:
- Monument Mountain – another great hiking option with a handful of trails to try
- October Mountain – largest state forest in Massachusetts with tons of hiking options
Lunch and Farm:
- North of Lenox – head to Whitney’s Farm Market & Garden Center to grab lunch at the deli (including gluten free sandwich options) and then hang out at the pumpkin patch. They had games, crafts, and tons of pumpkins to take home.
- South of Lenox – Grab lunch at a restaurant in Stockbridge (Once Upon a Table, Tiffany’s Cafe and Market, Main Street Cafe) then head to Windy Hill Farm for Apple picking.
Happy Hour and Dinner:
Our hotel has the cutest bar, so we had a happy hour drink there and struck up some other travelers.
Later, we went to dinner at Frankie’s. We had a great italian meal with plenty of gluten free options. The service was great and the food was delicious.
Day Three
Get Some Steps In:
With a long day of travel ahead, we wanted to start off the day with a little exercise and a last chance for leaf peeping. Right in Lenox, there is a wonderful park with wooded trails. After packing up and checking out, we hiked a couple miles in Kennedy Park. Make sure you pay attention to where you’re going because there is no service and lots of overlapping trails.
Coffee and Breakfast:
After our hike, we had breakfast at On a Roll Cafe. They had tons of great cafe food and coffee. It was busy but we didn’t have to wait long. If you want to wait until after breakfast for a walk, Kennedy Park is connected to the back of the parking lot. You could keep your car parked and just walk from the cafe!
Road Trip Stops Heading back to NYC:
Time to head home! We left some time for exploring on our way back to the airport in NYC, so we stopped at the following locations.
Olivia’s Overlook: My favorite view of the whole trip! This overlook is stunning with the fall colors and is just a quick pull out stop on the way to and from Lenox.
Hudson: We took a slight detour and stopped in Hudson for lunch. This is such a cool and artsy town, filled with shops, cute cafes, and art. This is a great roadtrip stop back to NYC.
