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The Berkshires, Massachusetts for Toddlers & Pre-K
4 day trip
Day 1
-
- History Museum
- Historical Landmark
Hancock Shaker Village
Pittsfield, MA
If not for the cars buzzing by on Route 20, you'd think you'd stepped into a completely different era. Ye Olde Village has vintage buildings showing how the Shakers used to sleep, eat, and do other things. ...
-
- Greek
- Italian
- Pizza
- Take-Out
Baba Louie's
Great Barrington, MA
You'll know this fabled crispy-crust, wood fired pizza place by the crowds of people spilling on to the sidewalk trying to get in....
-
- Historical Landmark
- Live Music Venue
Tanglewood
Lenox, MA
The picnickers start arriving an hour ahead of time, unpacking ginormous spreads with tablecloths, silverware, even candelabras (really!). Such elaborate concert-night dining is a tradition here, and it's a hoot to be part of. ...
-
- Hotel / Motel
Red Lion Inn
Stockbridge, MA
Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...
Day 2
-
- Boating
- Fishing
- Rafting
- Swimming
- Boat Ride
- Boat Tour
Wild 'N Wet Water & Sports Rentals
Lanesboro, MA
Who needs ocean surf when you've got crystal clear lake water to play in? Families love Lake Pontoosuc, a bustling place where pleasure boating is via motor, paddle, or foot....
-
- Art Museum
- History Museum
- Science & Nature Museum
- Special Collection
- Historical Landmark
- Aquarium
- Theater
Berkshire Museum
Pittsfield, MA
Kids love the "magic" entryway (doors open outward by themselves) and just about everything else at this landmark science-meets-history-meets-art kids' museum. Surprises are everywhere....
-
- Take-Out
- American
- Burgers
- Family Dining
Dakota Steak House
Pittsfield, MA
Ask for a family friendly place and locals will lead you here. The busy, log-cabin style eatery appeals to kids, with its hunting-lodge décor, extensive children's menu, overflowing plates, and a fabled Mud Pie for dessert. ...
-
- Hotel / Motel
Red Lion Inn
Stockbridge, MA
Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...
Day 3
-
- Special Collection
- Historical Landmark
- Roadside Landmark
- Train
Berkshire Scenic Railway Museum
Lenox, MA
Scenic rides aboard this mobile museum are in vintage 1920s cars, pulled behind a diesel engine run by an overalls-clad engineer. Excursions are the perfect length for little riders—about 30 minutes to Stockbridge, with a quick stop midway in Lee....
-
- Art Museum
- Special Collection
Norman Rockwell Museum
Stockbridge, MA
Paintings at this charming museum aren't just art: they're stories. Familiar even to kids, Rockwell is a perfect introduction to painting. The artist's intricately crafted details make viewing feel like you're peering through the window of a dollhouse. ...
-
- Hotel / Motel
Red Lion Inn
Stockbridge, MA
Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...
Day 9
-
- Art Museum
- History Museum
- Science & Nature Museum
- Special Collection
- Historical Landmark
- Aquarium
- Theater
Berkshire Museum
Pittsfield, MA
Kids love the "magic" entryway (doors open outward by themselves) and just about everything else at this landmark science-meets-history-meets-art kids' museum. Surprises are everywhere....
-
- Hotel / Motel
Red Lion Inn
Stockbridge, MA
Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...
The Berkshires, Massachusetts for Toddlers & Pre-K
4 day trip
Day 1
-
- History Museum
- Historical Landmark
Hancock Shaker Village
Pittsfield, MA
If not for the cars buzzing by on Route 20, you'd think you'd stepped into a completely different era. Ye Olde Village has vintage buildings showing how the Shakers used to sleep, eat, and do other things. ...
-
- Greek
- Italian
- Pizza
- Take-Out
Baba Louie's
Great Barrington, MA
You'll know this fabled crispy-crust, wood fired pizza place by the crowds of people spilling on to the sidewalk trying to get in....
-
- Historical Landmark
- Live Music Venue
Tanglewood
Lenox, MA
The picnickers start arriving an hour ahead of time, unpacking ginormous spreads with tablecloths, silverware, even candelabras (really!). Such elaborate concert-night dining is a tradition here, and it's a hoot to be part of. ...
-
- Hotel / Motel
Red Lion Inn
Stockbridge, MA
Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...
Day 2
-
- Boating
- Fishing
- Rafting
- Swimming
- Boat Ride
- Boat Tour
Wild 'N Wet Water & Sports Rentals
Lanesboro, MA
Who needs ocean surf when you've got crystal clear lake water to play in? Families love Lake Pontoosuc, a bustling place where pleasure boating is via motor, paddle, or foot....
-
- Art Museum
- History Museum
- Science & Nature Museum
- Special Collection
- Historical Landmark
- Aquarium
- Theater
Berkshire Museum
Pittsfield, MA
Kids love the "magic" entryway (doors open outward by themselves) and just about everything else at this landmark science-meets-history-meets-art kids' museum. Surprises are everywhere....
-
- Take-Out
- American
- Burgers
- Family Dining
Dakota Steak House
Pittsfield, MA
Ask for a family friendly place and locals will lead you here. The busy, log-cabin style eatery appeals to kids, with its hunting-lodge décor, extensive children's menu, overflowing plates, and a fabled Mud Pie for dessert. ...
-
- Hotel / Motel
Red Lion Inn
Stockbridge, MA
Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...
Day 3
-
- Special Collection
- Historical Landmark
- Roadside Landmark
- Train
Berkshire Scenic Railway Museum
Lenox, MA
Scenic rides aboard this mobile museum are in vintage 1920s cars, pulled behind a diesel engine run by an overalls-clad engineer. Excursions are the perfect length for little riders—about 30 minutes to Stockbridge, with a quick stop midway in Lee....
-
- Art Museum
- Special Collection
Norman Rockwell Museum
Stockbridge, MA
Paintings at this charming museum aren't just art: they're stories. Familiar even to kids, Rockwell is a perfect introduction to painting. The artist's intricately crafted details make viewing feel like you're peering through the window of a dollhouse. ...
-
- Hotel / Motel
Red Lion Inn
Stockbridge, MA
Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...
Day 9
-
- Art Museum
- History Museum
- Science & Nature Museum
- Special Collection
- Historical Landmark
- Aquarium
- Theater
Berkshire Museum
Pittsfield, MA
Kids love the "magic" entryway (doors open outward by themselves) and just about everything else at this landmark science-meets-history-meets-art kids' museum. Surprises are everywhere....
-
- Hotel / Motel
Red Lion Inn
Stockbridge, MA
Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...