Take this leaf-peeping tour through the state’s southern landscape

Editor’s note: This tour was originally published in 2018. It has been updated on Oct. 2, 2020, to reflect the many changes in business hours and operations since the start of the coronavirus pandemic. Correspondent Clover Whitham reported and wrote the original version of this tour.

© Submitted photo
Kathryn Kantorski of Fairfax took this shot in Wilmington several years ago.

The area around Bennington and Wilmington is highly popular with leaf peepers.

With good reason. Stunning vistas, scenic forest drives and visitor-friendly communities abound — and southwest Vermont is the first place most drivers from the New York City metropolitan area are likely to see while visiting the Green Mountain State.

Whether you are a denizen of Manhattan or Manchester, here is a leaf-peeping day trip you’ll enjoy.

Feel free to take any detours to lengthen or shorten this 60-mile, 90-minutes-of-driving loop. Any turn you make is sure to be picturesque.

Southern Vermont foliage tour: Driving directions

© ELIZABETH MURRAY/FREE PRESS
The Bennington Battle Monument — a memorial to a battle that took place across the state line, in New York.

Here’s an easy place to start: Look for the 306-foot-tall obelisk that stands at the height of the land overlooking the town of Bennington. The top of Bennington Battle Monument (15 Monument Circle, Old Bennington), finished in 1891, offers an excellent vantage point to view the valley and surrounding mountains.

Robert Frost’s grave: From there follow the tree-lined Monument Avenue past the historic homes to the Old First Church. The church, built in 1806, is adjacent to a cemetery where Robert Frost is buried and his headstone tells us he had “a lover’s quarrel with the world.” The unique swooping white fence and white church are a beautiful contrast to the colors of autumn. 

The Molly Stark Trail: From Bennington continue the historic journey by heading east up the mountain on Vermont 9, also called the Molly Stark Trail Scenic Byway. (Molly Stark, wife of Revolutionary War General John Stark, played a role in the success of the Battle of Bennington by recruiting and caring for soldiers).

Searsburg Mountain: Before Vermont 9 descends down to Wilmington, turn right on to Vermont 8 and climb Searsburg Mountain before twisting and turning your way down to Vermont 100. Take a right to Readsboro, a former mill town that straddles the Deerfield River. Iconic Route 100 twists its way along the river and on to Whitingham and north to Wilmington.

Charming Wilmington: In the center of Wilmington, (Main Street, Wilmington) shops and restaurants occupy historic buildings (or facsimiles rebuilt after fire or flood) that line the streets and hang over the river that cuts through town. 

Back over the mountain: Finish your leaf-peeping tour by climbing up and over the mountain on Vermont 9 west to Bennington. 

© Free Press photo
A stone marker outside the visitor center at the Bennington Battle Monument commemorates the Battle of Bennington of Aug. 16, 1777.

Smart stopping points

Bennington Battle Monument: 15 Monument Circle, Old Bennington,

Old First Church: This church’s cemetery is the site of poet Robert Frost’s grave, Old First Church, 60 Monument Ave., Old Bennington.

Downtown Wilmington: Shop and stroll in Wilmington. From art galleries to clothing, books to wooden bowls, there’s plenty to visit within walking distance of the intersection of Vermont 9 and 100. 

© Free Press photo
The cemetery at the Old First Church in Bennington, Vermont.

Where to eat in Bennington, Wilmington

Papa Pete’s: Locals and tourists rub elbows at the “home of the giant pancakes,” where you can dig into a flapjack the size of a pizza. Open for breakfast and brunch. Limited inside dining (reservations recommended); also outside seating and take-out options — call (802) 681-0181 for updates and details. At 1104 Woodford Road, Bennington.

Dot’s Restaurant: This establishment has been famous for decades, and not even the devastation of Tropical Storm Irene in 2011 could keep it down. Dot’s of Vermont has been rebuilt, and now the space is even more comfortable. The family-style breakfasts, lunches and dinners are as comforting, too. Inside dining and to-go options. At 3 W. Main St., Wilmington. Dial (802) 464-7284 for updates and details.

Markets, delis and cafes: A convenient way to rustle up a socially distanced, a-la-carte, take-out picnic breakfast, lunch, snack or dinner. Among those you might check out…

Around Bennington:

Around Wilmington:

For the kids

Woodford State Park: This park has easy hiking trails, including a 2.7-mile hike around a small lake, plus a sandy beach area and rowboats, canoes and kayaks to rent. 142 State Park Road, Woodford.

Molly Stark State Park: Here, you can walk the campgrounds, run around a play area and follow a hiking trail to a fire tower. Climb up the tower and take foliage selfies, 705 Vermont 9, Wilmington.

Best Instagram spots

Monument Avenue, Old Bennington: Whether a panoramic from the top of the Bennington Battle Monument or a close up of a foliage speckled catamount statue, you can’t go wrong on this street. (Between the Battle Monument, 1 Monument Circle, and the Old First Church, 60 Monument Ave.)

Red Mill Pond: The pond is just east of Woodford State Park (8570 Vermont 9, Woodford). The trees around the water here and edging the wetlands further east on Vermont 9 are the ones that tend to turn first. 

Searsburg Mountain: The apex of Vermont 8 in Searsburg is where you’ll find a cemetery and an informational sign for the wind turbines on the ridgeline above. 

Mt. Olga fire tower: From this tower located at Molly Stark State Park, 705 Vermont 9, Wilmington, you can see forests carpeted with color, for miles.

© Free Press photo
Wolf Kahn’s “November in Vermont,” 1977.

Contact Joel Banner Baird at 802-660-1843 or [email protected]. Follow him on Twitter @VTgoingUp.

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This article originally appeared on Burlington Free Press: Vermont fall foliage: Take this leaf-peeping tour through the state’s southern landscape