Driving on U.S. 4 Through Vermont from New York to White River Junction

Driving along U.S. Route 4 from the New York border to Interstate 89 in Vermont takes you on a scenic journey across the state's lush valleys, historic towns, and charming villages. This eastbound route, about 66 miles in total, traverses Bennington, Rutland, and Windsor counties and gives you a taste of both Vermont’s natural beauty and small-town charm. Here’s an in-depth look at the experience:
1. Starting Point: New York-Vermont Border near Fair Haven

As you cross the New York-Vermont border, you’ll enter the town of Fair Haven in Rutland County. Here, U.S. Route 4 becomes a divided highway, and Fair Haven welcomes you with classic New England scenery. This small town is known for its Fair Haven Town Green, where you can find historic architecture and a weekly farmers’ market in summer.

Fair Haven is also close to Lake Bomoseen, Vermont’s largest lake, and offers a glimpse of the Green Mountains in the distance. This town embodies a relaxed, rural atmosphere and marks the start of your journey through the scenic landscapes of Vermont.
2. Castleton

Just a few miles east, you’ll come to the village of Castleton, known for Castleton University—one of Vermont's oldest colleges, established in 1787. The campus adds a touch of collegiate charm to the village, which also boasts well-preserved historic buildings and a scenic backdrop.

If you have time, take a brief detour south to Lake Bomoseen, a popular recreational spot for boating, fishing, and swimming. This area is also rich in historic sites and quaint inns.
3. Rutland

Continuing east, U.S. Route 4 leads you directly into the city of Rutland, the largest town on this stretch of the highway. Known for its rich history as a former marble and railroad town, Rutland has a lively downtown with cafes, shops, and historic sites. Look out for Rutland’s Main Street and the Paramount Theatre, an iconic building from 1913 that hosts events and live performances.

Rutland is also home to Pine Hill Park, a popular destination for hiking and mountain biking, and Aitken State Forest, which offers stunning views of the surrounding valleys.
4. Mendon and Killington

Leaving Rutland, U.S. 4 climbs eastward into the Green Mountains, winding through the town of Mendon. The scenery becomes increasingly mountainous and forested, with long stretches of the route offering impressive views of Vermont’s natural beauty.

Continuing on, you’ll reach Killington, one of the most well-known ski resorts in the Northeast. Killington Resort is the largest ski area in the eastern United States and features multiple peaks, making it a major year-round destination for skiing, snowboarding, mountain biking, and hiking. During the fall, Killington is particularly breathtaking, as the autumn foliage blankets the mountainsides in vibrant colors.

Killington Peak is also visible from the road, offering panoramic views and popular trails. Route 4 in this section is dotted with inns, lodges, and restaurants catering to visitors, as well as local shops selling Vermont maple products and crafts.
5. Bridgewater and Woodstock

As you descend from the Green Mountains, the landscape begins to open up as you enter the towns of Bridgewater and Woodstock in Windsor County. In Bridgewater, look for the Long Trail Brewing Company, a classic Vermont brewery with a riverside location and a cozy pub.

Woodstock, one of Vermont’s most picturesque towns, is famous for its quintessential New England charm, with covered bridges, historic homes, and beautiful landscapes. Billings Farm & Museum and Marsh-Billings-Rockefeller National Historical Park are two notable landmarks. The national park is unique as Vermont’s only national park, preserving a working farm and promoting sustainable land stewardship.

Driving through Woodstock, you'll cross the Ottauquechee River, which winds through the village and has several lovely spots for photos and picnics. Woodstock’s historic downtown, lined with locally-owned shops, art galleries, and cafes, invites a leisurely stroll if you have time.
6. Quechee

Just east of Woodstock, Route 4 takes you to Quechee, another scenic village famous for Quechee Gorge, often called “Vermont’s Little Grand Canyon.” The gorge, carved by the Ottauquechee River, is about 165 feet deep and offers breathtaking views from the U.S. Route 4 bridge. This area is popular for hiking, and visitors can take a short trail down to the bottom of the gorge for a closer look.

Quechee is also home to the Simon Pearce glassblowing studio and restaurant, located in a historic mill building beside a restored covered bridge. Here, visitors can watch artisans at work, purchase unique glass pieces, and enjoy riverside dining.