Leaf peeping guide for Columbus Day weekend

Some suggested routes across western Massachusetts

(WWLP) – Columbus Day weekend is approaching, and that means that foliage is nearing its peak here in western Massachusetts. While you can see changing leaves along nearly every roadway in our region, here are a few routes you might consider taking if you’re looking to do some leaf peeping this holiday weekend.

If you have foliage photos, send them to us at reportit@wwlp.com!


  • Route 57 from Feeding Hills to Tolland provides a scenic ride along mountains, rolling hills, farmland, and charming town centers. The Granville Harvest Fair begins Saturday, and lasts through the weekend. You may want to continue on Route 57 past Tolland into Sandisfield (see Berkshire County).
  • Route 20 from Palmer to Brimfield is a lovely ride in the autumn. You may choose to continue east on Route 20 into Sturbridge, but first, you may want to detour down Route 32 into Monson or Route 19 into Wales as well.
  • Route 20 from Westfield to Chester brings you up along the Westfield River and through the foothills of the Berkshires, passing by the centers of Russell, Huntington (in Hampshire County), and Chester. You may wish to continue your journey into Becket in Berkshire County.
  • Route 202 from Holyoke to Westfield is a short, but scenic drive, which takes you down wooded hills in the Ashley Reservoir area and then by Hampton Ponds State Park. You may choose to continue up Route 10 into Southampton (in Hampshire County), or take Routes 10 and 202 south toward downtown Westfield.


  • Route 116 from South Hadley to Amherst passes by the campus of Mt. Holyoke College, Hampshire College, Amherst College, and Mt. Holyoke Range State Park; as well as several farms. You may wish to continue on Route 116 up to Sunderland (see Franklin County).
  • Route 47 from South Hadley to Hadley hugs the Connecticut River; passing through Hadley’s historic center, as well as numerous farms and Mt. Holyoke (Skinner Mountain). You may continue on Route 47 up to Sunderland (see Franklin County).
  • Route 9 from Northampton to Cummington takes you from bustling downtown Northampton (where the Paradise City Arts Festival is happening) through charming villages such as Leeds, Haydenville, Goshen, and Cummington. You may choose to pick up Route 143 in Williamsburg and head west toward Chesterfield and Worthington, and either take Route 112 back to Route 9, or continue west into Berkshire County.
  • Route 66 from Northampton to Huntington passes through quiet Westhampton, by tree-lined farmers’ fields. You can continue your journey onto Route 112, either north through the hills toward Worthington or south to meet Route 20 at the center of Huntington.
  • Route 9 from Amherst to Ware runs past wooded areas and scenic farmland toward the Quabbin Reservoir. You may wish to stop to see the changing leaves from the Winsor Dam or the tower at Quabbin Park on the Belchertown/Ware line.
  • Route 202 from Belchertown to Pelham passes through heavy woods in the Quabbin Reservoir watershed. You could continue up Route 202 into New Salem (see Franklin County).


  • Route 2, the Mohawk Trail, from Greenfield to Charlemont is for many people the quintessential autumn drive. Passing along the rapids of the Deerfield River, up mountains, and near the popular village of Shelburne Falls, the route is lined with small shops and farmstands, as well as foliage aplenty. Many drivers continue their ride into Florida in Berkshire County.
  • Route 2 from Greenfield to Orange may not get the same attention that the western portion of the route receives, but it is also provides a scenic fall drive. The dramatic French King Bridge traverses the Connecticut River between Gill and Erving, and the route continues along the Millers River until it splits with Route 2A in Orange.
  • Route 116 from Sunderland to Deerfield is a scenic route within itself, but it also connects some other lovely fall byways. You can continue on Route 116 south toward Amherst (see Hampshire County), or pick up Routes 5 & 10 in Deerfield.
  • Route 47 in Sunderland to Route 63 in Northfield stays along the east side of the Connecticut River past farmland, with views of Mt. Toby in the distance. Route 63 takes you through Montague and Millers Falls, and then along the Connecticut River again up through the center of Northfield.
  • Routes 5 & 10 from Whately to Bernardston passes by some of the Valley’s richest farmland and most popular attractions. Yankee Candle, Historic Deerfield, Magic Wings Butterfly Conservatory, and Kringle Candle are just some of the popular spots along the route, which also passes by shops and restaurants in downtown Greenfield.
  • Route 112 from Goshen (Hampshire County) to Colrain provides a lovely, quiet ride through the Berkshire foothills, crossing the Deerfield River near Shelburne Falls.
  • Route 116 from Deerfield to Plainfield (Hampshire County) takes you from Valley farmland to rolling hills, passing through the small towns of Ashfield and Plainfield. You may wish to continue into Savoy in Berkshire County.



  • Route 7 from Sheffield to Williamstown is a scenic ride through and through. The southern portion of the ride takes you through the upper Housatonic Valley with beautiful mountain views as you pass through Sheffield, Great Barrington, and Stockbridge. After meeting up with Route 20 and bypassing the center of Lenox (you can make a quick detour into the center) the route takes a more commercial character as it crosses into Pittsfield. The road moves past the shops and restaurants of downtown Pittsfield before passing alongside Pontoosuc Lake and again into the hills; passing by Mt. Greylock before entering picturesque Williamstown.
  • Route 2 from Florida to Williamstown is the Berkshires’ continuation of the Mohawk Trail. You can see Mt. Greylock in the distance after you go through the famous Hairpin Turn at the Florida/Clarksburg/North Adams line. Shopping and dining options are available in North Adams and Williamstown.
  • Route 8 from Sandisfield to Clarksburg crosses beautiful mountainous terrain, lakes, reservoirs, and quaint town centers. There are plenty of places to enjoy the beauty of nature along this route, from the Farmington River on the southern end to Mount Greylock on the northern end.
  • Route 57 from Sandisfield to Great Barrington climbs the Berkshires, moving through Sandisfield and New Marlborough, before meeting up with Route 23. You may wish to take Route 23 east toward Monterey and Otis, or continue toward Route 7 for the shopping and dining in Great Barrington.
  • Route 183 from Great Barrington to Lenox roughly follows the Housatonic River from Great Barrington through the village of Housatonic, and into Stockbridge and Lenox. Popular attractions, including the Norman Rockwell Museum and Tanglewood are along the way. You can also detour onto Route 102 to visit the center of Stockbridge or head toward Lee.
  • Route 20 from Becket to Lenox passes by campgrounds and mountain lakes in the eastern Berkshires. It then goes by the Lee Premium Outlets and Mass Pike Exit 2 before entering Lee’s historic town center, and continues on past Laurel Lake; meeting Route 7 in Lenox.

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