Great breakfast, be sure to get there before on time Saturday for breakfast, they switch to lunch at 11! We recommend the frittata and pancakes.
Upscale American breakfast & lunch cafe right in the heart of Lenox.
The best bagels in the area, really good!
An authentic french pastry shop and cafe right in the heart of Lenox.
Amazing ice cream! They also have grilled cheese sandwiches using chesse they make on site and you can visit the cows.
Great gourmet pizzas and salads right in the heart of Lenox.
Amazing chocolate and chocolate treats!
Relaxed pub with surprisingly good salads, open late.
Delicious quick service joint with popcorn chicken, popcorn cauliflower, tots, great salads and homemade soft serve.
Great craft cocktails, cheese boards, and tinned fish.
Abby’s parents favorite dinner spots. Delicious thoughtful dishes, be sure to make a reservation ahead of time if you’d like to go! They have a bar and a covered porch for outdoor dining.
New elevated restaurant by a chef from San Francisco.
A cute wine and tapas bar, where Josh and Abby had their first date!
A stylish chic inn with a bar lounge. Get the French 75 and the chicken tenders!
Wonderful italian food, get the pasta sampler and the balsamic blueberry glazed steak! They have locations in Florence, Italy and in the DC area as well.
Great, no frills indian food. Get the coconut saffron naan!
Delicious dinner spot.
Delicious mediterranean food, definitely recommend a reservation.
Abby and Josh’s favorite place in the Berkshires, we went there after we got engaged! A very special dinner that is a bit of drive but totally worth it! A three course meal for ~$75, the setting is a beautiful old house and the food is delicious.
A special dinner spot a bit of a drive but worth it!
This popular restaurant just re-opened. Farm to table food and craft cocktails.
A wonderful winery where Josh took Abby right after they got engaged! They have live music every weekend, a food truck and a bocce court. Abby’s parents spend most weekend visiting the winery and relaxing. The brunch is taking place at the refurbished barn on their property.
If the weather isn’t cooperating, this is a nice movie theatre. Bonus: you can bring Juju’s food into the theatre!
Great orchard right by Abby's parents house. They have cider and wine tastings and delicious cider donuts/pies.
A relaxed, grassy hike right near Balderdash Cellars.
A very popular hike in Great Barrington. Note that it gets busy on the weekends when the weather is nice.
A great loop train with 3-4 mile options.
Lovely 2 mile loop trail with beautiful views.
Abby and Josh's favorite hike! It's about 6 miles and 2-3 hours with a stunning view. Definitely a challenge but if you are up for it, you won't regret it!
Stunning gilded age mansion where Edith Wharton used to live. The grounds are amazing, with lush trees and flowers!
Take a tour to learn about amazing art and stories of Normal Rockwell, who was a local! You can also go visit his studio on the grounds. Highly recommend a visit.
Wonderful museum right by the Williams College campus.
Beautiful grounds and sculptures by Daniel Chesterwood who created the Lincoln Memorial.