On the Road: Fall Trip to the Berkshires

As I mentioned in Allie’s most recent update, we took a little road trip earlier this month to the Berkshires in Western Massachusetts to check on the leaves and partake in some fall fun.

(Yes, I know—#basic. But, I don’t care. I <3 this time of year, and I’m going to make sure that A and B do too).

We stayed in Pittsfield, which was about a five hour drive from Philly, and centrally located to all the places we wanted to visit. The suite-style property was ideal for traveling with A and B because it had extra space for them to play and a kitchen that was stocked with all the basics, so that we could make breakfast and dinner.

Enjoying hotel life

On our first full day in the area, we drove up to Mount Greylock, the highest point in Massachusetts. Had it not been so cloudy and windy, we would have had a better view from nearly 3,500 feet up. But, B enjoyed picking dandelions and tolerated my requests for photos, so it wasn’t a wasted venture.

Stopping at a scenic point on the way up

Obsessed with dandelions

It was windy up there!

On a clear day, you can see up to 90 miles away

We made a pit stop to visit some alpacas.

After a quick stop for lunch at Blueberry Hill Market and Cafe (located in New Lebanon, NY, which is basically just over the border from MA) we headed to the Harvest Festival at the Berkshire Botanical Gardens. All of the dreams that the girls never knew they had came true, when they got to jump into big piles of hay, and B had her face painted for the first time.

My little puppy

The next day was pretty rainy, but we ventured into downtown Pittsfield for brunch at Otto’s Breakfast and Deli. The entire town seemed deserted, but it turns out that’s because everyone had the same idea for brunch and was waiting for a table at Otto’s. A and B kept everyone entertained while we waited, and the omelettes were excellent.


Walking to brunch in the drizzle

After that, we did some more leaf peeping, and walked around Lenox, a cute little town filled with shops, art galleries, and delicious ice cream.

I wish the weather had felt more fall-like, but it was unseasonably warm and rained off and on during the weekend. But, we made the most of it and had a great time anyway—we are already talking about going back next year!