5 Best Covered Bridge Tours in Vermont This September

Vermont has more than 100 covered bridges—more than any other state in the country—and each one feels like a step back in time.

Built mostly in the 1800s, these wooden bridges are more than just functional; they’re symbols of rural New England charm.

September is one of the best months to explore them. Covered bridge tours let you combine history, photography, and scenic drives into one unforgettable Vermont experience.

Here are the five best covered bridge tours to check out this September.

1. Bennington County Covered Bridge Tour

Southern Vermont is a great place to start, and Bennington County is home to some of the state’s most famous covered bridges.

The Silk Road Bridge, Paper Mill Bridge, and Burt Henry Bridge are all close to each other, making it easy to explore them in one loop.

• Driving distance & duration: Around 12 miles, usually a 1–2 hour trip if you stop for photos.
• Route guidance: Start from downtown Bennington and loop along Route 67A toward the Battenkill River.
• Nearby attractions: Bennington Battle Monument, Old First Church, and small antique shops.
• Food stops: Don’t miss a maple creemee from a roadside stand or baked goods at Blue Benn Diner.
• Events in September: Bennington Garlic and Herb Festival is a fun stop if you time it right.

Driving here in September is especially pretty—the Battenkill River winds beneath many of the bridges, and the first touches of fall foliage make the scenery look like a postcard.

Pro Tip: Start your tour from downtown Bennington, where you’ll also find cafés and local shops to break up your trip.

2. Windsor County Covered Bridge Tour

If you’re looking for classic Vermont charm, Windsor County delivers.

This region has some of the oldest and most photographed covered bridges, including the Taftsville Covered Bridge in Woodstock and the Cornish-Windsor Bridge, one of the longest wooden covered bridges in the U.S.

• Driving distance & duration: About 20–25 miles, perfect for a half-day drive.
• Route guidance: Start in Woodstock, follow Route 4 east to Windsor, and loop back.
• Nearby attractions: Billings Farm & Museum, Quechee Gorge, and charming shops in Woodstock.
• Food stops: Simon Pearce restaurant by the falls or local cider mills for donuts.
• Events in September: Harvest fairs and farmers’ markets often pop up around Woodstock.

September is perfect here because Woodstock looks lively with harvest events and early foliage. The Ottauquechee River flowing under these bridges adds to the picture-perfect vibe.

Pro Tip: Park in Woodstock Village, stroll around, and then take short drives out to the bridges—this way you get both the town atmosphere and the scenic countryside.

3. Lamoille County Covered Bridge Tour

Up in northern Vermont, Lamoille County is where history meets adventure. The bridges here are close to Stowe and Smugglers’ Notch, which means you can easily combine your covered bridge tour with a scenic mountain drive.

• Driving distance & duration: Roughly 15 miles, about 2 hours with stops.
• Route guidance: Begin in Stowe and head along Route 100, branching onto backroads for bridge access.
• Nearby attractions: Stowe Mountain Resort, hiking trails at Smugglers’ Notch, and Mount Mansfield.
• Food stops: Piecasso for pizza in Stowe or cider tastings at Cold Hollow Cider Mill.
• Events in September: Stowe’s British Invasion car show is a big draw and adds fun to a fall trip.

The Gold Brook Bridge, also called “Emily’s Bridge,” is famous for its ghost stories, making it a fun stop in September as nights get longer and cooler.

The other bridges in the county are surrounded by peaceful farmland and backroads that feel untouched.

Pro Tip: Pair this tour with the Green Mountain Byway—it’s one of Vermont’s most scenic drives and connects perfectly with Stowe.

4. Caledonia County Covered Bridge Tour

For a quieter experience, head northeast into Caledonia County. This is where you’ll find some of the most authentic, less-touristy bridges.

The surrounding Northeast Kingdom region is already known for its untouched landscapes, and in September, the early foliage adds a warm glow.

• Driving distance & duration: Around 18 miles, typically 2–3 hours if you stop for lakeside breaks.
• Route guidance: Begin in St. Johnsbury and weave through the backroads toward Danville and Lyndon.
• Nearby attractions: Fairbanks Museum & Planetarium, Dog Mountain, and Joe’s Pond.
• Food stops: Local diners in St. Johnsbury or maple syrup stands along the byways.
• Events in September: Caledonia County Fair sometimes extends into early September, offering a true local vibe.

This tour feels more about the journey than the destination—you’ll be driving through small towns, farmland, and hidden corners of Vermont that most visitors never see.

Pro Tip: Bring a picnic basket and plan a stop near Joe’s Pond or Harvey Lake for a laid-back September afternoon.

5. Windham County Covered Bridge Tour

Windham County, located near Brattleboro, is another must-visit for bridge lovers. The Creamery Covered Bridge is one of the most popular in southern Vermont, and the county’s winding backroads make for a relaxing drive in early fall.

• Driving distance & duration: About 10 miles, a quick 1–2 hour loop.
• Route guidance: Start in Brattleboro and head north along Route 30, detouring for bridges.
• Nearby attractions: Brattleboro Museum, Retreat Farm, and local art galleries.
• Food stops: Stop for cheese at Grafton Village Cheese Company or grab fresh cider donuts.
• Events in September: Brattleboro Literary Festival and local harvest fairs add flavor to your trip.

September here is lively thanks to local fairs and farmers’ markets, so you can easily mix a bridge tour with stops for cider, cheese, and maple syrup.

Conclusion

Vermont’s covered bridges aren’t just wooden structures—they’re living pieces of history surrounded by some of the most beautiful scenery in New England. And September is the perfect time to experience them.

Whether you choose the historic bridges of Windsor County, the quiet corners of Caledonia, or the lively charm of Bennington, these tours let you slow down and enjoy Vermont at its best.

Read More: 5 Best Scenic Drives in Vermont for September