This post contains affiliate links.

Much to our delight, fall arrived late in the Northeast this year. On this particular late October morning, temperatures in New York started at a balmy 55 degrees and only warmed up throughout the day, reaching the mid-70s during the afternoon in Vermont. Had this been an average autumn, we would have missed most of the peak foliage, but the Hudson Valley of New York, southern Vermont, and New Hampshire were in their prime! We could not have timed this portion of the trip more perfectly!

The morning of day two was mostly driving again, but we were treated with gorgeous views outside the windows as we pressed northward up the New York Thruway. Bright yellow and orange trees lined the pavement with scattered exposed boulders and Catskill peaks in the distance. Add very light Sunday morning traffic and this was one of the most pleasant highway drives of the trip.

Near Albany, we left the interstate and changed course to the east towards Vermont on country roads. Shortly after entering the boys’ first new state of the trip, we stopped at the Arlington Covered Bridge. Built in 1852, it is one of Vermont’s oldest remaining covered bridges and its classic, beautiful red exterior is straight out of a picture postcard. After exploring the edges of the river, we noticed picnic tables sitting in the grass beside the adjacent white-steepled church and took advantage of this most picturesque and perfect New England setting for lunch.

A nearby house was home to Norman Rockwell in the 1940’s and he completed many paintings in his art studio including his Rosie the Riveter, based on a neighbor right here in Arlington. A covered bridge and Norman Rockwell history certainly made this first stop the perfect welcome to Vermont.

We made quick progress across the state to the town of Windsor, home to the American Precision Museum. The museum is housed in a mid-19th century factory where precision interchangeable parts were first used. The factory was a significant supplier of rifles during the Civil War and military battles beyond. The museum includes historic machines and tools such as sewing machines and typewriters among the building’s original water-powered machines and drill presses.

While small, we easily spent an hour at this very well done museum. Building stations kept Jasper occupied while hands on activities for kids throughout held Gavin’s attention long enough for Mom and Dad to enjoy the displays. Volunteers were helpful and placards explained every display thoroughly.

Several blocks away, the Cornish-Windsor Bridge crosses the Connecticut River into New Hampshire. This two-span bridge is the longest covered bridge in the country and over 150 years old! We admired this beautiful structure and took our requisite New Hampshire welcome sign photo before heading back across the bridge to Vermont. With only two hours of sunlight remaining, we still had many towns to see before calling it a day.

Heading south, we veered off the interstate again (although I-91, as it hugs the river among rolling hills and forests, is one of the most beautiful sections of interstate we’ve ever driven!) in search of more quaint towns. Our route took us through Grafton, as iconic as a New England town could possibly be. Although the white-steepled church at the center of town was occupied with a wedding party, we enjoyed Main Street with its brightly colored trees, waving American flags, and fall potted mum decor.

The road out of town led us to Townshend, whose town common is featured as Redbud in the Chevy Chase movie Funny Farm (cue the deer). Daylight was fading fast when we arrived in Newfane where three white-steepled buildings – the courthouse and two churches – looked out on the town common. This trip originated with the goal of seeing small New England towns coated in fall colors and these towns with their commons and churches did not disappoint!

As night fell, we arrived in Brattleboro where we stopped for a take-out dinner from the Vermont Country Deli before continuing on to eat in our hotel room across the river in New Hampshire.

Vermont in the Fall