Our weekends of fall getaways continue, this time in Lenox, Massachusetts. My fiance and I had to attend a wedding in the Berkshires, which we were thrilled to go to because a) it didn’t involve air travel (we’d hopped on planes for so many weddings over the summer and b) because we’d been meaning to check out the famous Berkshires, but never really had a reason to visit.
So, we rented a car, and inside two hours we were in Lenox, one of the villages in the extremely charming Berkshires, an area known for country roads, great restaurants, an epic outdoor summer concert series and charm.
We got in early on a Friday in order to do some exploring. Here’s an itinerary for your trip to Lenox. (So, each weekend, we’ve been getting away to great spots three hours or less from Manhattan. (You can read our other posts on fall getaways here and here)
Day 1:
Explore the area: I could not get enough of the rolling hills, farms and beautiful homes as we drove through Lenox on our way to drop off our bags at the hotel to explore. From there, we headed into their Main Street of sorts, checking out the beautiful architecture and ivy-clad historic homes.
Wine at Alta Wine Bar: We spent a lot of time on the windy road that many of the bars and restaurants in Lenox are located on. There were so many cute places to pop into before a much-anticipated dinner later in the evening. We came across Alta, a restaurant and winebar, and it looked so inviting that we decided to pull up to the bar and enjoy some glasses of wine.
We loved that they offer wine flights, by different varieties. We decided on two glasses of Malbec that turned into another round before we headed to dinner.
Dinner at Bistro Zinc: Next, we walked to Bistro Zinc for some delicious French fare in a beautiful setting. We loved the elegant vibe and the copper-plated roof and white tablecloth service.
We sat down at a great table in a corner window and were greeted by the restaurant’s manager, who treated us with meticulous attention the entire night. We started the night with two cocktails of his concoction based on cues we gave him. I said spicy, not sweet and my fiance said whiskey-based. We were greeted with a tequila cocktail with a great spiciness that was almost too easy to drink and a whiskey-based manhattan type of cocktail with a smokeyness to it. We were off to a good start.
Next, we ordered an appetizer to share: the duck confit rolls with hoisin sauce and sweet chilli glaze. For our entrees, I had a roasted halibut on a bed of spinach with a rich and creamy sauce, it was the special of the day. My fiance had the pork schnitzel which was prepared with lingonberry jam, cucumber-potato salad and a meneue sauce.
This meal was accompanied by a bottle and a half of wine, at the manager’s recommendation. They were both complex, and different, really complimenting the delicious meal we had just enjoyed. We will absolutely be returning on our next trip to the Berkshires.
Day 2:
Brunch at Haven Cafe: Haven is an institution in Lenox. This small cafe doesn’t take reservations, so brace yourself for a wait, but trust us when we say it is worth it.
When you walk inside, you’ll be tempted by the array of pastries, cakes, brownies and other fresh-baked sweets behind the counter where you’ll order. Because of wedding planning, we skipped the sweets.
We ordered two large iced coffee, and I got the Haven omelette, which is filled with feta, spinach and tomatoes. My fiance got the granola and yogurt. The food and coffee were great, and we loved the quaint, hometown feel of the restaurant.
Dinner at Wheatleigh: The wedding we attended was at the beautiful Relais & Chateau Hotel, Wheatleigh, which dates back to 1893 and is set on 22 acres. The couple who was getting married rented the estate for the entire weekend, so we also went there the night prior for cocktails.
Wheatleigh is an expensive hotel to stay in at nearly $1,000 per night, but if you visit Lenox, it is worth having dinner and drinks on the property, which is so grand.
We had tons of hor d’oeuvres, filet mignon and roasted veggies, all of which were just delicious.
Day 3:
Apple Picking & Wine Tasting: With the fall air crisp, we set out to do my favorite fall activities: Apple Picking. We drove ten minutes away to Hilltop Orchards, which grows 26 varieties of apples ready for picking. We filled up one large bag (which we are still eating today, using in salads and such) and then headed to their barn for some wine tastings.
We did a wine tasting, picking seven of their varieties to try. We chose a mix of hard ciders, wines and their famous ice wine. The ice wine and some of the ciders were by far our favorites. Then we picked up some fresh apple cider donuts before heading home to Manhattan!
Read Our Other Fall NYC Getaway Guides:
Travel Guide: Beacon, New York
Fall Travel Guide: Mohonk Mountain Resort
Fun Fall Outings Outside of NYC