For some, fall is the best time of year, with temperatures finally dropping, leaves turning all shades of color, and restaurants and bars offering autumn-based items (including dishes and drinks made with pumpkin, which tends to evoke all kinds of emotions—not all of which are good—but that’s another topic for another day).
Sure, the Greater Boston area is a great place to be in October, but sometimes it’s nice to get out of town and experience what the rest of the region has to offer. Since there are so many options, the burning question is, where to go?
You could basically head in any direction and find some good places, but some routes in particular are just meant for the fall season. Below are 10 good ones, with some food/drink options along or near each one.
Route 6A, Cape Cod
Northern New England tends to get much of the press when it comes to fall road trips, but this winding old road is easily one of the most scenic in all of the Northeast—especially when the leaves start to turn. Heading east from the Sagamore Bridge, Route 6A meanders through such historic villages as Sandwich, Barnstable, Yarmouth, Dennis, and Brewster, with each having its own personality and all having extremely old trees that come ablaze this time of year.
[Restaurant Options: the Sagamore Inn in Sagamore (by the Sandwich line) for seafood and Italian dishes in a homey space; Grumpy’s in Dennis for breakfast dishes, sandwiches, and other comfort food]
Route 77, Southeast Corner of Rhode Island
Roads that end at the water tend to be special routes for everyone from motorcyclists to roadtrippers to mystery riders, as they tend not to have too much traffic because they don’t really go anywhere. And this surprisingly rural road near the Massachusetts border is a perfect example of this, going through historic Tiverton Four Corners and bucolic old Little Compton before petering out by an often-wild stretch of the ocean in Sakonnet. There are few places in New England that feature both farmland and ocean views, and this is certainly one of them.
[Restaurant Option: The Commons Lunch in Little Compton (just off Route 77) for classic “South Coast” and Rhode Island fare, including calamari and jonnycakes]
Route 169, Northeast Corner of Connecticut
When you take a night flight from, say, Boston to Washington, DC, you’ll find very few truly dark stretches of land below, as nearly the entire route flies above major cities and sprawling suburban areas, with one of the only dark areas being where this road can be found. The lightly traveled Route 169 makes its way up and down high hills and through farmland while heading into such unspoiled towns as Woodstock, Pomfret, and Brooklyn, and it is so beautiful that it has actually been designated a National Scenic Byway.
[Restaurant Options: The Vanilla Bean Cafe in Pomfret for sandwiches, desserts, and live music at night in a tree-shaded hilltop setting; Sharpe Hill Vineyard and Fireside Tavern in Pomfret (just off Route 169) for wine tastings and a romantic special-occasion meal in a hillside spot in the middle of nowhere]
Route 5, Pioneer Valley of Massachusetts
Valleys seem to be particularly great places to view foliage, and this very old byway makes its way through a particularly gorgeous one just east of the Berkshires. Here you’ll find spectacular scenery that includes Sugarloaf Mountain in South Deerfield, Mount Tom in Easthampton and Holyoke, historic Deerfield Village, and much more, while bustling Northampton is a good stop if you’re hungry or thirsty. Some great foliage routes lead off of Route 5 as well, including the Mohawk Trail (Route 2) and Route 116.
[Restaurant Options: The People’s Pint in Greenfield for farm-to-table food and house-brewed beer; Packard’s in Northampton for cheap drinks in a rustic space; Tom’s in Whately for hot dogs, burgers, and ice cream in a rural setting]
Route 4, Central Vermont
While not a particularly long stretch of road, the section of Route 4 between Quechee and Killington is one that you could spend days on, especially in the fall. This east-west route goes through some of Vermont’s most memorable places, including the aforementioned Quechee, with its interesting shops and deep gorge that’s often seen on New England calendars; Woodstock, which some call the prettiest town in New England; and Killington, which is a legendary ski area that also happens to have tremendous foliage.
[Restaurant Options: Worthy Kitchen in Woodstock for some of the best burgers in New England and—wait for it—Hill Farmstead beer on tap; Ramunto’s in Bridgewater for excellent pizza and local beers in a comfortable space within a historic mill]
Route 100, Vermont
A legendary byway that runs from the Massachusetts line all the way up to the Canadian border, Route 100 really deserves its own article because there’s so much to see here. Expect unforgettably classic Vermont scenes from start to finish, including lots of exploring around Wilmington, a ski town near the southern end; Weston, a tiny mountain village that’s home to the Vermont Country Store; Plymouth, a historic town with jaw-dropping views everywhere; Waitsfield and Warren, two valley towns with a mix of farmland and forests; Waterbury, a beer lover’s paradise; and Stowe, a quaint village that’s a four-season resort.
[Restaurant Options: SoLo in South Londonderry for a true farm-to-table experience well off the beaten path; American Flatbread in Waitsfield for outstanding wood-fired pizza in a farmhouse setting; Prohibition Pig in Waterbury for BBQ and Southern-style food along with a variety of Vermont beers]
Route 49, Waterville Valley, New Hampshire
There aren’t too many “box canyons” in New England, but Waterville Valley is about as close as you’ll get to one, with towering mountains surrounding the village that basically cause Route 49 to end right in town (though you can take a couple of very rough mountain roads out of Waterville if you dare). A relatively short route from Route 93 in Campton to this quiet resort community, the road features peaceful river views much of the way along with deep forests, and it all tends to open up as you reach the village, with memorable views nearly everywhere as the road comes to a stop.
[Restaurant Options: Mad River Tavern in Campton for classic American fare in a cozy space; Coyote Grill in Waterville Valley for New American fare in a casual upscale environment]
Route 112, White Mountains, New Hampshire
While nearly all of Route 112 is worth checking out, the stretch of road between Lincoln and Conway is what most people are familiar with, as the Kancamagus Highway (which this part is typically called) is often considered the most scenic road in all of the Northeast, and almost feels intimidating in a way, since it goes through miles of untouched wilderness with no gas stations, shops, or any development at all. While not exactly an undiscovered road, the “Kanc” has a number of turnoffs where you can quickly get away from the crowds and check out various waterfalls, rivers, and mountain views without having to walk far.
[Restaurant Option: Woodstock Station in North Woodstock for classic American fare and house-brewed beer in a sprawling structure with multiple rooms]
Route 302, White Mountains, New Hampshire
Some of the most dramatic scenery in New England can be found on—or just off—this remote road that also extends into Vermont to the west and Maine to the east in the northern part of the Whites. Perhaps the best stretch for fall foliage lies between Twin Mountain (where it meets Route 3) and North Conway (where it veers off from Route 16), with mind-blowing views in the Zealand area, Bretton Woods, Crawford Notch, Bartlett, and Glen, including some parts around the notch that feel more like mountainous areas in the western part of the US.
[Restaurant Options: Yesterdays in Jackson (a few miles north of Route 302) for hearty breakfasts; White Mountain Cider Co. in Glen for New American fare in an old farmhouse; Moat Mountain in North Conway for BBQ and house-brewed beer]
Route 9, South Coast, Maine
A short stretch of road that can be confusing to follow, this route may not have views of towering mountains or verdant farmland, but during peak foliage season, it certainly competes well with the roads above. From Route 1 in Wells, Route 9 makes its way to Kennebunkport, a beautiful old shipbuilding town and summer resort with huge old elm and maple trees lining the side streets, then it cuts through Cape Porpoise, a working fishing village with some of the best seaside views in Maine. The road skirts scenic Goose Rocks Beach and Biddeford Pool, then returns to Route 1 briefly before heading to Ocean Park, a charming tree-shaded family-style summer community, and Old Orchard Beach, which retains its tacky but charming honky-tonk feel.
[Restaurant Options: The Ramp in Cape Porpoise for drinks, pub grub, and American classics in a lively old local bar with views of the water; Mabel’s in Kennebunkport for lobster rolls, blueberry pie, and water views across the street]