6 Country Roads Near Boston That Are Pure Bliss In The Fall

Follow Main Street/Boylston Street in a loop around Wachusett Reservoir through the towns of Clinton and West Boylston. There are 37 miles of shoreline and although you can’t go on the water (it’s a key source of drinking water), this rural setting is tranquil and there are plenty of trees that blaze with color in autumn.

This route connects places that are integral to U.S. history, and the road happens to be heavily lined with trees, making it a delightful drive to do in fall. From Lexington, take Massachusetts Avenue to MA 2A, pausing at Minuteman National Historical Park. Visit Concord, then head down Walden Street to Walden Pond. This route is just shy of nine miles long.

Pick up on MA-135 and prepare for a relaxing 17-mile drive along this road. The route takes you past the Wellesley Campus, which is surrounded by beautiful trees. At Natick, pause at Cochituate Lake State Park, a vast area with three connected ponds and an abundance of foliage. The leaf peeping opportunities don’t end there; Ashland State Park is another highlight of this drive and, once in Hopkinton, it’s easy to add a visit to Hopkinton State Park to your itinerary.

Visit the largest cranberry grower in the world, right here in Massachusetts! This 15-mile drive begins in Plymouth on Federal Furnace Road, which leads you past Myles Standish State Forest. Make a left onto Cranberry Road – if you’d like to hike through the forest, you can use this as an access point. Otherwise, make a right on Federal Road and cruise along until you reach your destination: A. D. Makepeace Company, which has been producing cranberries for 160 years! It’s best to take this drive on October 19, 21, or 28, 2017 because that’s when public harvest tours of the bog are held.

This 90-mile drive features stunning scenery at almost any time of year, but as fall progresses, the summertime crowds thin in the North Shore beach towns. This makes strolling along the sand a more peaceful experience. Although this is a coastal route, you travel through numerous wooded sections of road that really shine in autumn.

If your favorite part of fall is orchards, then you’ll want to take a drive through Apple Country. This 15-mile route connects four orchards. Start at Berlin Orchards (located at Route 62 and Lower Sawyer Hill Road) for maple syrup, honey, gourds, and apples. From there, head to Honey Pot Hill Orchards (138 Sudbury Road, Stow), where you’ll find three hedge mazes and cider donuts galore. Continue onto Carver Hill Orchards (101 Brookside Avenue, Stow), which offers a country store, pick-your-own produce, and ice cream. Finally, conclude your mini apple fest at Bolton Spring Farm (149 Main Street, Bolton). Browse this quaint country store, which offers cider donuts, apple cider, apple dumplings, and pick-your-own pumpkins.