The Perfect Itinerary for a Day Trip to The Berkshires

A few weeks ago I planned an itinerary for a day trip to Lenox, Massachusetts in the Berkshires for my Mom’s birthday. It was such a relaxing, beautiful day and I wanted to share it with you all!

What I love about the Berkshires is if you’re in the New England area it’s such a great weekend escape. It’s only a two-hour drive from Boston, and just under three hours if you’re coming from New York City.

Here is the perfect itinerary for a day trip to the Berkshires.

xx, Heather

Pick One Town to Explore

“The Berkshires” actually encompasses several towns in the area, so you’ll want to choose one to focus on for a day trip. In this case, we spent the day in Lenox which ended up being a great choice, with plenty to do and see.

The Perfect Itinerary for a Day Trip to The Berkshires

Grab Breakfast at Haven Cafe

Haven Cafe is a popular spot cafe in Lenox with grab-and-go or seated options. They pretty much serve everything you could want, from sandwiches and salads to the full range of breakfast fare like eggs, pancakes, etc. If you’re a matcha lover like I am, they also make a great matcha latte.

Another cute spot, if you’re looking for an easy coffee and pastry, is Lenox Coffee. In addition to the homey cafe inside, they have a cute patio with a few tables for outdoor seating.

Visit Edith Wharton’s Estate - The Mount

If you follow me on Instagram, you’ve seen me posting about this lately. This was by far my favorite part of the day. We ended up spending more time here than I thought we would, which was great. Once you buy your ticket for The Mount, the estate is pretty much yours to explore as you wish. You don’t have to do a guided tour of the home, but we did and I really enjoyed learning about Edith Wharton’s life, the home she designed, her writing, and would definitely recommend it! After that, you can explore the grounds surrounding the house. We lucked out with a beautiful day and spent a few hours in the gardens. There are also walking trails in the woods. We wandered these a little bit on the way out.

The Perfect Itinerary for a Day Trip to The Berkshires. The Mount.

Try the Local Wines at Hilltop Winery

There are quite a few wineries in the area and in the surrounding towns, but if you’re trying to keep the driving to a minimum (as we were), Hilltop Orchards, home of Furnace Brook Winery, is a great choice near Lenox. I’ve been here twice now and the owners never disappoint with their generosity and kindness. The winery sits on an apple orchard so they have lots of apple-themed goodies as well. Do the wine tastings, buy a bottle of your favorite, and a few of their cider donuts, and sit outside near the orchard. It’s the perfect place to enjoy the rest of the afternoon.

Shop on Main Street in Lenox

Save an hour or so before dinner to explore the shops in town. Make sure you stop in Oliva!, a gourmet olive oils & vinegar store where everything is up for grabs as a tasting. The peach white balsamic vinegar is SO good. Design Menagerie was another favorite shop of mine. They had beautiful clothes and home goods.

Have Dinner at Alta Wine Bar

If you’ve spent the day in Lenox, this is the perfect spot for dinner - right on Main Street in the village. This was my second time at Alta Wine Bar, but the first time having dinner. Their menu always has great local and organic ingredients. The restaurant has a very cozy feel and is bigger than it looks when you first walk in; there are two additional rooms past the wine bar and entryway dining area. In the summer, they also have tables on the front porch.

If You Choose to Spend the Night

If you chose to spend the night in town there are some gorgeous gilded-age homes that are now hotels and resorts. Last year I stayed at The Cranwell Inn which is absolutely beautiful. It has a full spa, golf course, and restaurant for dinner as well. Another great option is Blantyre. Both of these are perfect for a special occasion in the Berkshires and really set the tone for the rich history of the area.

I’ve been to Lenox a few times now, and would love to hear other recommendations for the Berkshires if you have them!