Driving Tours around Brattleboro and Southeastern Vermont

We have put together three driving tours for you to enjoy while visiting the area. The tours cover a significant portion of southeastern Vermont and will show you a good overview of the villages, their history and the geography that shaped them. The mileage and times shown are approximate. You will find plenty more to see and do, so relax, take your time and enjoy the ride! If you would like to print this to bring along with you, be sure to download the accompanying map (on another page).

Red Route
Brattleboro - Newfane - Townshend - W. Townshend - Wardsboro - Dover - Wilmington - Marlboro - Brattleboro 3-6 hours (Click Here to download the accompanying map)

Begin the Red Route by taking Route 30 northwest from Brattleboro along the West River. In West Dummerston, about 5 miles, you will see the Dummerston Bridge - longest covered bridge in the State that is still in use. Just as you begin to enter Newfane you will see the Windham Historical Society on your right. This is an interesting and nicely presented vignette of the area’s history.

In the village of Newfane you will see one of the most picturesque town centers in the state. It is worth parking and walking around this perfect little taste of a bygone time. Just north of the Newfane Common is the 1884 Vermont National Bank building (now Chittenden Bank). The bricks were brought in by ox cart. Bricks for the front were 5’, 3’ for sidewalls and 2’ for the back for a total cost of $6,650. Inside some old features remain, including the butternut counter and wrought iron grillwork at the tellers’ windows.

Continuing up Route 30, you will come to Townshend and its often photographed Common with church, white houses and schools. Just outside of Townshend you will encounter the Scott Bridge. It is 277 feet long and no longer in use. Up the hill is the Townshend Dam and recreation area. After crossing the dam you can take a left and parallel Route 30 on the other side of the West River. You will come to Townshend State Park with its hiking and camping.

The next town on Route 30 is West Townshend, the ancestral home of William Howard Taft. A side trip from here brings you up a steep hill to the town of Windham. The church in Windham is the second highest in the state, exceeded only by the church in Woodford, Bennington County.

After West Townshend, you will turn left on Route 100 heading west. Up to this time, you have been following the West River Valley. Now you will begin climbing up into ski country. You will note the much smaller villages as the flat farm land of the valley is left behind. You will drive through North Wardsboro, Wardsboro, Wardsboro Center and start heading south on 100 in West Wardsboro. Here you are in the headwaters of the Deerfield River and ski country. Heading south on 100 you will begin to see Mount Snow and to encounter the distinctive feel of a ski resort.

The Mount Snow/Deerfield valley is loaded with recreational opportunities summer and winter. Continuing south you will come into Wilmington. The town’s strategic location, halfway between Bennington and Brattleboro keeps the town center busy with traffic. Strolling among the charming homes and businesses in Wilmington is an enjoyable way to spend an afternoon.

Heading east on Route 9, you are headed back toward Brattleboro. You will barely be able to tell that you are passing through Marlboro except for the signs. The little town center is just off of Route 9. This is the site of the famous Marlboro Music Festival each summer and Marlboro College, a small liberal arts college. Before coming into Brattleboro, you will pass through West Brattleboro. When coming into Brattleboro, you will enter via Western Avenue. This broad street passes by some of the loveliest examples of 19th century house architecture in the region. (End of the Red Route Tour )

White Route
Brattleboro - Newfane - Townshend - Grafton - Saxtons River - Bellows Falls - Westminster - Putney - Brattleboro (Click Here to download the accompanying map)

Take Route 30 to Townshend (see additional details of this portion in the Red Tour). You will pass by the Dummerston Bridge across the West river. Here you can stop and get a closer look at the recently restored bridge.

Newfane is the County seat of Windham County. In 1825 the town was moved from Newfane Hill to its current location. The commanding county courthouse was built in 1825 when the town resettled. There is a festival on the town Common each fall. Just past the town center is the well-known Newfane Flea Market held on Sunday mornings from May through October. Parking is a challenge - be careful and be patient.

In Townshend you will be struck by the town Common with its gazebo, fountain, schools and the church - built in 1790. The town was settled in 1764. Fair Day in August is for the benefit of Grace Cottage Hospital (see page 53). The Townshend Pumpkin Festival is held the first weekend after Columbus Day.

Turn right off Route 30 onto Route 35 to Grafton. Take note that the road forks after about 4 miles. Take the left fork to Grafton. The town was given the name Grafton in 1792. There have been restorations to many of the buildings in town by the Windham Foundation. There are cross country ski trails and a small covered bridge near the cheese factory as you enter town. The famous Grafton Band, featured in their 4th of July parade and other town events, was started in 1867.

Route 121 out of Grafton takes you through Cambridgeport, Saxtons River and Bellows Falls - all villages of Rockingham. After Cambridgeport the next small town is Saxtons River. The main street is worth a stop. On the north side of Main Street is Vermont Academy, founded in 1876.

Established in 1802, Bellows Falls has one of the oldest paper mills built in Vermont. In 1835 production of silk was begun but the mulberry groves which fed the silk works were killed by a severe winter. The site was a favorite camping place for the Abenaki Indians.

Examples of their pictographs are found near the foot of the Connecticut River falls. Downtown is interesting for walking and shopping. Be sure to take a look at the newly restored Exner Block with its artists’ studios and galleries along one of the first canals in the United States.

Rejoin Route 5 south to Westminster. This restful village lies on a mile-wide river flood plain. March 1775 is the date of the Westminster Massacre - a confrontation between New York court officers and the local settlers over who controlled ownership of the land. In this fracas William French was killed. His well-known grave is in the old cemetery in the north part of Main Street. At the convention held in Westminster in January, 1777, Vermont declared itself a free and independent state, remaining so until joining the Union in 1791.

Continuing south on Route 5, be sure to look out for Harlow’s Sugar House about 3 miles north of Putney. Putney is known for it many schools (Putney School, Landmark College, The Grammar School, etc.) and for an abundance of artisans and artists. In the town center the Town Hall houses the historical society museum. Right behind here is the internationally known Sandglass Theater, renowned for their amazing puppetry. Other well-known features in Putney include Basketville and the Yellow Barn School of Music.

Continuing south toward Brattleboro on Route 5 you'll pass farms and houses that line the banks of the Connecticut River. (End of White Route)

Yellow Route
Brattleboro - Guilford Center - Green River - Halifax - Jacksonville - Whitingham - Marlboro - Brattleboro (Click Here to download the accompanying map)

Take Route 5 south (Canal Street) out of Brattleboro. About one mile past Exit 1 of Interstate 91 turn right at the Guilford Country Store toward Guilford Center. Guilford Center consists of an 1837 church, a Grange Hall, library, historical society and several houses. Continue for about a half mile and bear to the right toward Green River. The Green River covered bridge, the simple church and the historic crib dam (recently restored) are all worth a more leisurely look.

In Green River, bear right at the church, before you go over the bridge, and continue about 2 miles. Turn left at the intersection for West Halifax. There is a historical society building here and a Grange that is well known in the area for their public suppers.

Continue into Halifax by following signs for Route 112 to Jacksonville. Halifax is the birthplace of Brigham Young. Continuing into Jacksonville, the North River Winery (pictured below) is right in town along with the well known Stone Soldier Pottery studio and shop.

If you continue on past the winery you can bear left on Route 100 south. Continue for 1.5 miles and turn left on Town Hill Road. Go to the top of the hill and there is a monument to Brigham Young in a field away from the road. The area hosts a public picnic area and a tremendous view of the surrounding mountains and Lake Sadawga. Down the hill toward the lake brings you to Route 100 again. Turning left to Whitingham there is a historical society museum. Returning to Route 100 north brings you to Jacksonville and eventually to Route 9 east to Marlboro and Brattleboro.

At the intersection of Routes 100 and 9 is an outdoor summer weekend flea market. A few miles east toward Brattleboro on Route 9 is Hogback Mountain with a spectacular view. Use caution here. There are often pedestrians on this heavily travelled road.

Heading east on Route 9, you are headed back toward Brattleboro. You will barely be able to tell that you are passing through Marlboro except for the signs. The little town center is just off of Route 9. This is the site of the famous Marlboro Music Festival each summer and Marlboro College, a small liberal arts college. Before coming into Brattleboro, you will pass through West Brattleboro. When coming into Brattleboro, you will enter via Western Avenue. This broad street passes by some of the loveliest examples of 19th century house architecture in the region. (End of the Yellow Route Tour )