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The site of a military outpost built in 1724, Brattleboro is the Byway's most southerly Waypoint and now one of its largest urban centers. Its cosmopolitan atmosphere was established in the 19th century by a mineral springs resort that attracted travelers to a promised "water cure" and continues today thanks to the School for International Training, whose students and teachers come from many countries. A vibrant downtown that celebrates the performing and visual arts is focused along a Main Street that follows the curve of the adjacent Connecticut River. Brattleboro declares it can provide "all of Vermont, close to home."

Brattleboro is the Waypoint community for an area that includes the towns of Vernon, Guilford, Dummerston, and Putney, VT, and Hinsdale, Chesterfield and Westmoreland, NH. Plans are underway to create a Waypoint Interpretive Center in the River Garden, located on the banks of the Connecticut in the center of this vibrant community.

The designated Byway routes in the Brattleboro area are Routes 5 and 142 in Vermont and Route 63 in New Hampshire.

Nature & SceneryPhoto by Bob Linck
The exposed rock and forested slopes of New Hampshire's Mt. Wantastiquet create a dramatic backdrop for Brattleboro's downtown, and includes trails of the Mt. Wantastiquet State Forest. The Connecticut is joined to the south of town on the New Hampshire side by the Ashuelot River and to the north on the Vermont side by the West River, where a large cove, known as the Retreat Meadows, is a gathering place for migratory waterfowl on the Connecticut River flyway. For more about birding and nature observation in the Brattleboro area, visit the Connecticut River Birding Trail.

The Belle of Brattleboro (802-254-1263), an excursion tour boat that operates seasonally, offers river tours of the Connecticut and a portion of the West River. The Bonnyvale Environmental Education Center is a strong voice for resource protection in the region.

In addition to the Connecticut River Scenic Byway routes, New Hampshire has a listing of other
scenic drives.
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The Brattleboro Farmers' Market is one of the oldest in the region, and is supported by a wide range of producers from the area who grow vegetables, fruits, berries, and flowers, and organic meats. The Brattleboro Retreat Farm is a conserved working dairy farm that includes a "petting zoo" of farm animals.

Brattleboro celebrates its agricultural heritage on the first Saturday in June with an annual "Strolling of the Heifers" parade and festival through the historic downtown. This internationally renowned parade and festival -- the Green Mountain State’s light-hearted version of Spain’s Running of the Bulls -- has been named one of Vermont’s “Top Ten Summer Events.”

Across the river in Keene, Stonewall Farm is a working New England farm and non-profit education center, dedicated to promoting the importance of local agriculture and the stewardship of natural resources.

Contemporary sheep farming now includes milking sheep to produce specialty cheeses. Award winning-sheep cheeses are made and ripened in a "cheese cave" at
Vermont Shepherd, in Westminster, near Putney, VT. In the Brattleboro area you can buy many agricultural products directly from the producers. You can pick up Christmas trees at Wilson's Tree Farm in Putney, or visit a working dairy at the Robb Family Farm in West Brattleboro. Dessert puddings are the specialty of Echo Farm in Hinsdale. The eagerly anticipated Cheshire Fair in nearby Swanzey, NH, draws spectators and participants to the animal competitions, displays of fruits, vegetables, and crafts, and the sights and sounds of farm life past and present.

Farmers Markets | Farm Stands and Pick Your Own | Farm Stays
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culture At the cultural heart of Brattleboro – itself a regional cultural center – is the Brattleboro Museum & Art Center. A few steps away is the Art Deco Latchis Theater, which houses a movie theater, hotel, restaurant and brewery all under one roof. The Brattleboro Music Center, a dance school, a childrens' theater and other local theater companies all offer a lively schedule of performances. The downtown is an historic district with plenty of restaurants and bookstores.

The city of Keene, NH, just east of the Byway, is another regional cultural center. Among its attractions are the
Colonial Theater and the Apple Hill Center for Chamber Music. For more information about the arts, contact the Grand Monadnock Arts Council (603-357-3906, 800-639-9029), the Horatio Colony Museum (603-352-0460) and the Thorne-Sagendorph Art Gallery at Keene State College (603-358-2720).
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Fort Dummer was the earliest European outpost north of the present Massachusetts border, built in 1724 during a period when armed conflict with Native Americans persisted all over New England. The fort was abandoned, but settlers returned in the late 1700s to establish a community along the Whetstone Brook. It blossomed with the growth of industries like the Estey Organ Company, the world's largest manufacturer of reed organs, which in 1880 employed more than 500 and made more than a quarter million organs before pianos eclipsed their popularity.
Brattleboro's architecture is well represented in several National Register Historic Districts. Visit the Brattleboro Historical Society and the Guilford Historical Society.

historic markers in the area offer a glimpse into the past, where tangible reminders remain or where events may have passed without a trace.

Two historic steel bridges from the early 20th century span the Connecticut River between Brattleboro's downtown and Hinsdale. Covered bridges in the Brattleboro region of Vermont include the Creamery Bridge over Whetstone Brook, the Green River Bridge in Guilford over the river of that name, and Vermont's longest covered bridge, the
West Dummerston Bridge over the West River.
New Hampshire covered bridges in the area include four in Swanzey that span the Ashuelot River: the Slate Bridge, the West Swanzey Bridge, the Sawyer's Crossing Bridge, and the Carleton Bridge. Two more covered bridges over the Ashuelot are in Winchester – the Ashuelot Bridge and the Coombs Bridge.

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The Vernon Dam on the Connecticut River creates a pool or low-current area that extends north beyond the mouth of the West River. The West is popular with canoeists and kayakers. A ski jump in Brattleboro draws international competition.
The region is home to a growing number of hiking trails. Mt. Wantastiquet itself is a popular hiking destination. The Connecticut River Joint Commissions provide a
map of river access points in the Mt. Wantastiquet Region.
Canoes and Kayaks are for rent at the Vermont Canoe Touring Center (802-257-5008) located at the confluence of the Connecticut and West Rivers, at 451 Putney Road, where the Veterans Bridge crosses the West River.

State parks in the area include:
Fort Dummer State Park, Brattleboro
Pisgah State Park, Chesterfield
Chesterfield Gorge Natural Area, Chesterfield

For more about Recreation on the Connecticut River Byway
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Brattleboro’s Union Station was among the last generation of major railroad passenger stations built in Vermont. It was constructed of stone in 1915-1916 for the Central Vermont and Boston and Maine Railroads. The station is now home to the Brattleboro Museum & Art Center. Amtrak maintains an office on the ground floor adjacent to the tracks.

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Products, Lodging, Dining, Services & Local Links

productscall 1-877-CTBYWAY for more information


Brattleboro Chamber of Commerce

Southern Vermont Regional Marketing Organization

Monadnock Travel Council

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Farmers Markets

Brattleboro Area Farmers’ Market
Two locations: Rte 9, West Brattleboro, Saturdays 9am-2pm. Also on Main St., Merchants Bank Square, Brattleboro, Wednesdays 10am-2pm, mid-June - September. Linda Dierks, 802 254-8885.

Keene Farmers' Market
Commercial parking lot off of Gilbo Ave., Keene, NH. Tuesdays & Saturdays, May-October, 9am-2pm. Fruits, vegetables, herbs, plants, flowers, syrup, honey and baked goods. Rain or shine, 603-835-6722.

Farmstands, Pick Your Own, Farm Stays

Elysian Hills Tree Farm
Bill & Mary Lou Schmidt
209 Knapp Road, Dummerston, VT 05301
(Off Rte. 5, between Exits 3 & 4, I-91)
802 257-0233
Organic rhubarb, Gilfeather turnip seed, Wholesale/Retail

Mountain Mowings Farm
Mary & Randy Hickin
1999 Black Mountain Road, Dummerston, VT 05301
April - December
Blueberries, raspberries, strawberries, vegetables, perennials, jams, pickles, Farm Stand, PYO

Walker Farm
Jack, Karen & Kristin Manix
1190 US Route 5, East Dummerston, VT 05346
April 7 - Thanksgiving
Blueberries, raspberries, strawberries, choice container plants & heirloom vegetables, farm stand

The Blueberry Haus
Dan & Brenda Knock
809 Guilford Center Road, Guilford, VT 05301
July & August
802 257-0068
Blueberries, Farm Stand, PYO

Green Mountain Orchards
The Darrows
West Hill Road, Putney,VT 05346
Mid-July thru mid-October
Blueberries, apples, farm stand, PYO

Harlow’s Sugar House
Donald W. Harlow
563 Bellows Falls Road, Putney, VT 05346
(3 mi north of Putney Village on Route 5)
March 1 - December 31
Blueberries, raspberries, strawberries, apples, farm stand, PYO

The Scott Farm and Naulakha
Dummerston, VT
The Sugarhouse at the Scott Farm sleeps 2 people and pets are welcome. The Dutton Farmhouse sleeps 8 people - no pets at this property and children are most welcome. Just down the road is Naulakha, the former home of Rudyard Kipling. This is a Trust property which sleeps 8 people. Mr. Kipling loved children and he would be happy to know that they are still welcome at his home today.

Sweet Tree Farm
East Dummerston, VT
(802) 254-4634 Email:
Tucked back behind a stand of trees and surrounded by scenic pastures, our vacation rental offers total peace and quiet. A two bedroom house which features a well-equipped kitchen and cable TV. The best way to contact us is by e-mail.

The Apple Place
Roger Bienvenu
781 Old Walpole Rd., Surry, NH 03431
10am-6pm, daily, August 25-October 25
Apples: Paula Red, Macintosh, Cortland & Macoun

Farmstead Acres
Marshall & Pati Patmos
143 London Rd., Westmoreland, NH 03467
9am-4pm, Friday-Sunday, Thanksgiving weekend-Christmas
Cut-your-own Christmas trees: balsam fir, white spruce, Scotch & white pine; wreaths, roping, greens, crafts & decorations

High Hopes Farm
Joanne & Bruce Smith
582 Glebe Rd., Westmoreland, NH 03467
8am-6pm, daily, July-Christmas
Pick your own, wholesale, and retail: raspberries (July), blueberries (mid-July through August to early September)

Inn at Valley Farms B&B and Cottages
Walpole, NH
E-mail: Working organic farm complete with an elegant 1774 Colonial home offering antique-furnished rooms with private baths and gourmet candlelight breakfast using our own organic fresh eggs and produce. Farm also offers two three-bedroom cottages and a farmhouse perfect for families, small groups or extended stays. Visit our farm animals, collect eggs, and pick produce, edible flowers, and herbs from our extensive gardens in season or just relax in this tranquil setting. Hiking, great views, extensive orchard, fine dining, and some of the world's best chocolate just minutes away.


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Historic Markers

Here, in Brattleboro, was located the world’s largest manufacturer of reed organs. For more than a century, reed and pipe organs made in Brattleboro were sold to homes and churches around the world. The unusual slate-sided factory complex on Bridge Street and the adjacent Esteyville neighborhood were developed in the early 1870s. Philanthropic and civic-minded, the Estey Company patented many manufacturing improvements and was a pioneer in equal pay for women.
Located on Canal Street, U.S. Route 5, opposite end of Bridge Street.

Brattleboro, VT – ‘NAULAKHA’: Rudyard Kipling’s home
Rudyard Kipling’s home near Brattleboro for 4 years after marriage to the American, Caroline Balestier, and after visiting her home, famed British writer built isolated ‘Naulakha’. Here he wrote the ‘Jungle Books’ and other stories, and two daughters were born. In 1896 the Kiplings returned to England.
Located on U.S. Route 5, North of Brattleboro.

One and one-half miles south on Route 142 is the marker for Fort Dummer, built in 1724, becoming Vermont’s oldest permanent white settlement. The actual site is now flooded by the water from the Vernon Dam.
Located near Railroad station.

Guilford, VT – ROYALL TYLER: Early American Playwright
Boston-born Royall Tyler’s play, ‘The Contrast’ was the first American drama to be performed in this country (1787) and his novel, ‘The Algerine Captive’ presented the first Yankee types in our literature. He came to Guilford in 1791 and was Chief Justice of the Vermont Supreme Court for 9 Years.
Located on U.S. Route 5, at Guilford Center

Connecticut Valley Route
On this former wilderness trail to Canada, the pioneers built old Fort Dummer in 1724 below Brattleboro, then the frontier’s most advanced outpost. Guilford, then the largest town in Vermont, was the scene of bitter strife between the ‘Yorkers’ and the Green Mountain Boys led by Ethan Allen.
Located on U.S. Route 5, near Massachusetts state line.

Born October 11, 1872, in a modest cottage 1.7 miles west of here on Horseshoe Road. Stone graduated from Amherst College and Columbia Law School, returning to the latter as Dean, 1910-1924. Attorney General of the United States in President Coolidge's Cabinet, he was appointed a justice of the Supreme Court in 1924, and Chief Justice in 1941, serving until his death April 22, 1946. A teacher, lawyer, judge and judicial craftsman of the highest order, he held the affection and respect of the lawyers of the nation.
Located on NH 63, at its intersection with the Old Chesterfield Road in the village of Chesterfield.

In 1772, "the people called Methodist" held their first religious meeting in this state on the James Robertson farm, 1.2 miles north of here, on Christian Street, with Philip Embury as the preacher. On June 20, 1803, Francis Asbury spoke here using as his text: "Let us run with patience the race that is set before us."
Located on the north side of NH 9, about 1 mile west of its junction with NH 63.

In the Holman and Merriman Machine Shop opposite this location, George A. Long of Northfield (Mass.) in 1875 built a steam-propelled four wheel automobile with a fifth wheel for steering. This vehicle, fired by hardwood charcoal, had a bicycle-type frame, ordinary wooden wheels, solid rear axle and could maintain 30 miles per hour, roads permitting. This early inventor patented and built another automobile, propelled by gasoline, now in the Smithsonian Institution.
Located at a parking lot on the south side of NH 119, about .2 mile east of its junction with northbound NH 63.

About 150 feet north of here stood the famous Hampshire Pottery Works, founded by James Scolly Taft for the manufacture of earthenware. In 1878 Majolica ware was a major product, followed in 1883 by the addition of useful and decorative art objects and souvenir pieces. With the introduction in 1904 of the famous "mat glaze," Hampshire Pottery was recognized as a leader in its field.
Located in front of the Keene Public Works Office Building on lower Main Street.

The first of two famous Keene glass factories was established near this site in 1814 and produced window glass for the New England area until 1853. Another glass works (1815-1842), 1.5 miles southeast of here on Marlboro Street, made bottles and flasks now known as "Keene Glass" and prized today by museums and collectors.
Located on the east side of Washington Street at Fuller Park.

Swanzey, NH – DENMAN THOMPSON (1833-1911)
A famous theatrical trouper who lived and died in West Swanzey. He gained a national reputation by his portrayal of the character, "Joshua Whitcomb," the New Hampshire farmer on a trip to Boston. From this he subsequently evolved "The Old Homestead," a play of long runs before enthusiastic audiences.
Located in a small triangular plot at the junction of NH 32 and West Swanzey Road, opposite Monadnock Regional High School.

This church, built on the northeast corner of Cole Cemetery in 1762, was moved in sections by ox cart in 1779 to this location, then known as Federal Hill. A steeple with a bell cast by the Paul Revere Foundry was added in 1826. This edifice is recognized as one of the most beautiful churches in New England.
Located on the north side of NH 63 in the Park Hill section of Westmoreland, in front of the Meeting House.

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Connecticut River Byway Council