Mary’s guidebook and Things to do!
Favorite Places to Visit
Hikes, Museums, Music and Dance!
While we are recovering from Covid-19, I decided to add lots of hiking and outdoor places that families can visit while still social distancing.
Great Spring, Summer and Fall hike for all levels. Full moon kayaking and eagle watching. Bring the kids!
45 locals recommend
Bartholomew's Cobble Reservation
105 Weatogue RdGreat Spring, Summer and Fall hike for all levels. Full moon kayaking and eagle watching. Bring the kids!
Local waterfall and great for a picnic with the kids. Stop at The Marketplace for a wonderful prepared lunch and then go and have fun!
33 locals recommend
Umpachene Falls Park
Umpachene Falls RoadLocal waterfall and great for a picnic with the kids. Stop at The Marketplace for a wonderful prepared lunch and then go and have fun!
This is what people come to the Berkshires to see. It never disappoints. Grab folding chairs in my front hall closet then go in the afternoon and sit on the lawn listening to the rehearsals. Bring a lunch or have lunch in Lenox at Bistro Zinc. Any reason to go to Tanglewood is a good reason. Guided tours and the on-site museum are all a must!
398 locals recommend
Tanglewood
This is what people come to the Berkshires to see. It never disappoints. Grab folding chairs in my front hall closet then go in the afternoon and sit on the lawn listening to the rehearsals. Bring a lunch or have lunch in Lenox at Bistro Zinc. Any reason to go to Tanglewood is a good reason. Guided tours and the on-site museum are all a must!
Skiing
It’s been many years since I last skied here. It’s close by and has a sledding slope for the kids and non-skiers.
39 locals recommend
Butternut Basin
It’s been many years since I last skied here. It’s close by and has a sledding slope for the kids and non-skiers.
Catamount Mountain Ski Resort
78 Catamount RdJust a ten minute drive away!
Hiking
There are many hikes within miles of my home. Many are listed here in my Guidebook but you can google the top rated hikes in the Berkshires and make it a day!
This is a wonderful drive on Mt Washington and a great hike for all levels. For the kids and easier hike for all drive to the lower parking lot and hike in. The upper hike can be steep.
282 locals recommend
Bash Bish Falls State Park
Falls RoadThis is a wonderful drive on Mt Washington and a great hike for all levels. For the kids and easier hike for all drive to the lower parking lot and hike in. The upper hike can be steep.
Just 5 minutes away from my home are several entrances. If you’re a strong hiker then plan to go via Mt Washington for spectacular views.
17 locals recommend
Appalachian Trail
Appalachian National Scenic TrailJust 5 minutes away from my home are several entrances. If you’re a strong hiker then plan to go via Mt Washington for spectacular views.
Benedict Pond Loop Trail is a 2.7 kilometer loop trail located near Great Barrington, Massachusetts that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Bring a lunch and use the picnic tables near the lake and entrance.
20 locals recommend
Benedict Pond Loop
Benedict Pond Loop Trail is a 2.7 kilometer loop trail located near Great Barrington, Massachusetts that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Bring a lunch and use the picnic tables near the lake and entrance.
Basin Pond
4-22 Becket RdBreathtaking views of Stockbridge and a great country drive! To have a wonderful country drive, set your GPS for West Stockbridge then again set it for Olivia’s overlook and you’ll love the drive there. Then continue down to Stockbridge.
51 locals recommend
Olivia's Overlook
Hiking TrailsBreathtaking views of Stockbridge and a great country drive! To have a wonderful country drive, set your GPS for West Stockbridge then again set it for Olivia’s overlook and you’ll love the drive there. Then continue down to Stockbridge.
Stevens Glen Trail is a 1 mile moderately trafficked loop trail located near West Stockbridge, Massachusetts that features a waterfall and is good for all skill levels. The trail is primarily used for hiking, walking, nature trips, and snowshoeing and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.
Stevens Glen Road
Stevens Glen RoadStevens Glen Trail is a 1 mile moderately trafficked loop trail located near West Stockbridge, Massachusetts that features a waterfall and is good for all skill levels. The trail is primarily used for hiking, walking, nature trips, and snowshoeing and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.
Clam River
I’ve not hiked this yet but it is top rated.
Steadman Pond
Housatonic Flats Reserve
439 Stockbridge RdDance
This is totally unexpected and well worth the drive. I prefer the 2 pm matinees so I can combine a great country drive. Only do this drive in the daylight hours. You will need to follow route 7 for evening performances. (For matinees, Follow these directions carefully.) Go down Maple Ave in Sheffield approximately one mile then set your GPS to Otis MA. Take your time and enjoy. Once you arrive in Otis, set the GPS for Jacob’s Pillow and have a wonderful scenic drive. This drive will take 30 minutes at a fast clip so leave one hour before a performance to enjoy the drive. Astounding talent! Very memorable.... This place will not disappoint!
257 locals recommend
Jacob's Pillow
358 George Carter RdThis is totally unexpected and well worth the drive. I prefer the 2 pm matinees so I can combine a great country drive. Only do this drive in the daylight hours. You will need to follow route 7 for evening performances. (For matinees, Follow these directions carefully.) Go down Maple Ave in Sheffield approximately one mile then set your GPS to Otis MA. Take your time and enjoy. Once you arrive in Otis, set the GPS for Jacob’s Pillow and have a wonderful scenic drive. This drive will take 30 minutes at a fast clip so leave one hour before a performance to enjoy the drive. Astounding talent! Very memorable.... This place will not disappoint!
Museum
I've taken guests here many times and I never get tired of going. Many visiting artists on showcase. Arrive in time to catch a guided tour. You’ll be happy you did. To get there from Sheffield, set your GPS for Housatonic then add the museum and enjoy the scenic drive.
344 locals recommend
Norman Rockwell Museum
9 Glendale RdI've taken guests here many times and I never get tired of going. Many visiting artists on showcase. Arrive in time to catch a guided tour. You’ll be happy you did. To get there from Sheffield, set your GPS for Housatonic then add the museum and enjoy the scenic drive.
This is a world class museum and about a hour away but well worth the effort. Plan the whole day and also see the MassMOCA in North Adams. Start with the Clark then have lunch in Williamstown. Mass MOCA is 15 min away and you can do both. Wear comfortable shoes.
329 locals recommend
The Clark Art Institute
225 South StThis is a world class museum and about a hour away but well worth the effort. Plan the whole day and also see the MassMOCA in North Adams. Start with the Clark then have lunch in Williamstown. Mass MOCA is 15 min away and you can do both. Wear comfortable shoes.
Surprisingly wonderful to visit and experience. See the Clark Museum, have lunch in Williamstown then go to MassMoCA. What a day!!!!
44 locals recommend
Mass MoCA Way
Mass MoCA WaySurprisingly wonderful to visit and experience. See the Clark Museum, have lunch in Williamstown then go to MassMoCA. What a day!!!!
Maple Corner Farm
794 Beech Hill RdCatamount Mountain Ski Resort
78 Catamount RdNaumkeag
5 Prospect Hill RdExcellent Dining all year
Great small cozy bar with a full or bar menu. Enjoy local chatter and experience a well established spot.
This would be one of your favorite restaurants if you lived in the southern Berkshires!
75 locals recommend
Old Mill
53 Main StThis would be one of your favorite restaurants if you lived in the southern Berkshires!