Hilltop Heights - Guide to the Berkshires
City/town information
Mass MoCA, Berkshire Art Museum, Massachusetts College of Liberal Arts, great restaurants!
33 locals recommend
North Adams
Mass MoCA, Berkshire Art Museum, Massachusetts College of Liberal Arts, great restaurants!
Williamstown
Home of Williams College
Adams
Quaint downtown with restaurants and shops, home of Mount Greylock!
Pittsfield
The largest city in the Berkshires with plenty of restaurant options!
Charming Vermont town with Revolutionary War battle monuments and a great music, arts, and beer scene!
61 locals recommend
Bennington
Charming Vermont town with Revolutionary War battle monuments and a great music, arts, and beer scene!
Lenox
Historic town known for Tanglewood and its EXCELLENT restaurant selection!
Clarksburg
Rural Berkshire town with great views of the mountains and plenty of parks!
Lee
Quaint and walkable downtown with premium shopping outlets nearby
Stockbridge
Picturesque home of Americana artist Norman Rockwell.
Waterfalls and a canal featuring a State Park with a great visitor center showcasing local wildlife and the history of industry along the canal.
Turners Falls
Waterfalls and a canal featuring a State Park with a great visitor center showcasing local wildlife and the history of industry along the canal.
Sightseeing
Hike or drive to the top of the tallest mountain in Massachusetts!
213 locals recommend
Mount Greylock
Hike or drive to the top of the tallest mountain in Massachusetts!
MASS MoCA
1040 Mass MoCA WayMassachusetts Museum of Contemporary Art
Great area for walking, hiking, swimming, kayaking, and picnicking!
11 locals recommend
Clarksburg State Park
1199 Middle RdGreat area for walking, hiking, swimming, kayaking, and picnicking!
Come visit the only natural white marble bridge in North America!
74 locals recommend
Natural Bridge State Park
McAuley RoadCome visit the only natural white marble bridge in North America!
Beautiful campus surrounded by the Berkshire Mountains on all sides. Great for outdoor walks and enjoying a coffee at one of the nearby cafes.
42 locals recommend
Williams College
880 Main StBeautiful campus surrounded by the Berkshire Mountains on all sides. Great for outdoor walks and enjoying a coffee at one of the nearby cafes.
Ski resort only half an hour away in charming Charlemont!
107 locals recommend
Berkshire East Mountain Resort
66 Thunder Mountain RdSki resort only half an hour away in charming Charlemont!
Hike the Berkshires along the Deerfield and Cold Rivers!
15 locals recommend
Mohawk Trail State Forest
Cold River RoadHike the Berkshires along the Deerfield and Cold Rivers!
Historic birthplace of women's suffragist Susan B Anthony.
20 locals recommend
Susan B. Anthony Birthplace Museum
67 East RoadHistoric birthplace of women's suffragist Susan B Anthony.
Rocky waterfalls and rapids in downtown Shelburne Falls. See the waterfalls while dining along the Deerfield River!
54 locals recommend
Shelburne Falls
Rocky waterfalls and rapids in downtown Shelburne Falls. See the waterfalls while dining along the Deerfield River!
Outdoor adventure park with rafting, ziplines, and more!
78 locals recommend
Zoar Outdoor Adventure Resort
7 Main StOutdoor adventure park with rafting, ziplines, and more!
Mount Snow
Excellent Vermont skiing about 45 minutes north of Hilltop Heights
Quick and easy trail hidden within North Adams - you will be rewarded with waterfalls!
31 locals recommend
Cascade Trail
22 Brickyard CtQuick and easy trail hidden within North Adams - you will be rewarded with waterfalls!
Hancock Shaker Village
1843 W Housatonic StLiving history museum, great for kids and families.
Norman Rockwell Museum
9 Glendale RdMuseum filled with iconic artist's works.
Art museum on the Williams College campus containing contemporary art, photography, prints, and Indian painting
78 locals recommend
Williams College Museum of Art
15 Lawrence Hall DrArt museum on the Williams College campus containing contemporary art, photography, prints, and Indian painting
Jiminy Peak
37 Corey RdSki resort in Hancock, MA
Prospect Mountain Ski Area
204 Prospect Access RdGreat for beginners and cross country skiing!
Monument to Revolutionary War battle with elevator to top. Excellent views, and close to Old Bennington.
72 locals recommend
Bennington Battle Monument
15 Monument CirMonument to Revolutionary War battle with elevator to top. Excellent views, and close to Old Bennington.
At the top of the hairpin turn on Route 2, experience AMAZING views of MA, VT, and NY while having a coffee and shopping at the gift shop. Do not miss!
6 locals recommend
Wigwam Western Summit
Mohawk TrailAt the top of the hairpin turn on Route 2, experience AMAZING views of MA, VT, and NY while having a coffee and shopping at the gift shop. Do not miss!
Food scene
Our favorite restaurant for date night; excellent meals and cocktails in North Adams
94 locals recommend
PUBLIC eat+drink
34 Holden StOur favorite restaurant for date night; excellent meals and cocktails in North Adams
413 Bistro
40 Main StreetFun new bistro with great food and drinks in North Adams
Enjoy your meal with the best view of the Berkshires nestled on a switch-back road in Clarksburg
17 locals recommend
Golden Eagle Restaurant
1935 Mohawk TrailEnjoy your meal with the best view of the Berkshires nestled on a switch-back road in Clarksburg
Local brewery in the Mass MoCA complex with some great flavors!
56 locals recommend
Bright Ideas Brewing
111 Mass MoCA WayLocal brewery in the Mass MoCA complex with some great flavors!
Alta
34 Church StExcellent French menu! (Note - this is in Lenox)
Bistro Zinc
56 Church StFabulous French dining (Note - this is in Lenox)
Renee's Diner
780 Massachusetts AveThe best breakfast in town!
Grazie
26 Marshall StHearty Italian food in downtown North Adams
Desperados
23 Eagle StGreat Mexican food in downtown North Adams
Jack's Hot Dog Stand
12 Eagle StA local institution!
NARA SUSHI
139 Ashland StreetGreat sushi spot in downtown North Adams
Freight Yard Restaurant & Pub
1 Furnace StExcellent burgers and beer list in North Adams
Chef's Hat
905 Simonds RdGreat breakfast diner in Williamstown
Cozy restaurant with craft cocktails and savory meals - great for date night in Williamstown
24 locals recommend
Gramercy Bistro
16 Marshall StCozy restaurant with craft cocktails and savory meals - great for date night in Williamstown
Our favorite pizza in North Adams - great crust and specialty pizzas
18 locals recommend
Ramuntos Brick Oven Pizza
67 Main StOur favorite pizza in North Adams - great crust and specialty pizzas
Traveler advice
What to pack
Winter in the Mountains
Winter in the Berkshires can get very cold and very snowy. Quick snowfall can make roads quite slick, even with good plowing. Driveways, roads, and walkways get quite slippery, so please be extra careful outside! Bring a warm coat, hat, and gloves!