Mileage between sites is bracketed, in bold and given in miles and tenths of miles, e.g. (2.6) for two and six tenths, or (0.1) for one tenth of a mile. The exception to this rule is the mileage for the full extent of SIDE TRIPS, which is neither bracketed nor bolded.

Municipalities are listed by letters in the guide and on markers; sites and historic areas are identified by numbers.

Sites visible from the Routes are in caps within the text.

Side Trips and other Off Route attractions are suggested at points marked by an asterisk (*) and italics. Directions to these sites are at the end of each tour. Because basic tours take several hours each, we suggest return visits to explore these additional sites. Dutchess County Farm Produce Maps and winery brochures are available at Tourism Information Centers county-wide.

Telephone numbers in Dutchess County are primarily in the 845 area code, with the exception of Millerton and Pine Plains, where some numbers are in the 518 area. Check the telephone directory for assistance.

Where the map indicates "Start" set your trip meter at "0" and begin. (Note that individual trip meters may vary slightly from mileage indicated.)

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(62 Miles, 2.5 Hours) START.
The tour starts at the (I) Rt. 199 off the Taconic Parkway. Drive 1.0 mile to the entrance of Wilcox Park. Rt. 199 was the route of the Salisbury Turnpike, an 18th c. stage and transportation route from Connecticut to the Hudson River.

1 WILCOX PARK (R). The route from the Taconic Parkway passes Wilcox Park, a public county park.

Drive 5 miles to Lake Rd. Turn right on Lake Rd. and drive 3.1 miles to Route 82, bearing left around Stissing Lake.

2 STISSING MOUNTAIN (R). 1403 ft. high, is used as an observation/fire tower. Those hearty enough to brave the access trail (R) can see the entire Hudson Valley on a clear day.

Lake Rd. bypasses Pine Plains hamlet, skirting the shores of three lakes, headwaters of the Wappingers Creek: Thompson Pond, a “forever wild” nature preserve and registered national landmark since 1974; Twin Island Lake, once called “Mud Pond”; and Stissing Lake. Trees frame a view of STISSING MT. (L).

Turn right on Rt. 82 South and drive 1.7 miles to Strever Farm Rd.

3 MASHOMAC FISH AND GAME PRESERVE (R). A former dairy. Early roads known by name linked farms to markets.

Turn left on Strever Farm Rd. and drive 0.3 mile to Bethel Cross Rd. Bear left on Bethel Cross Rd. and drive 0.6 mile to Carpenter Hill Rd.

4 MORAVIAN MONUMENT (Y). Constructed in 1859 in memory of Christian missionaries who tried to convert Shekomeko Indians.

Turn left on Carpenter Hill Rd. and drive 0.5 mile to stop sign, CR 83. Turn left at stop sign and drive 1.8 miles to Rt. 82.

This area was home to the family of 18th c. historian Isaac Huntting.

5 ROWE FAMILY BURIAL GROUND (R), part of the Old Round Top church cemetery, was settled ca. 1740 by Lutherans in Bethel Hamlet.

The road passes homes of early families, who built the town and local industry.

Turn right onto Rt. 82. Drive 0.6 mile to light.

6 WILBER CLOCK TOWER (L) is a familiar landmark. STISSING HOUSE (L), still a restaurant, began serving the public in the 18th c.; marker opposite records the first Stissing Log House Tavern (1782) (L). The hamlet of Pine Plains invites exploration of off-route sites, shops, restaurants. Street parking.

Cross at light to CR 83A and drive 0.2 mile to Maple St. Turn right on Maple St. and drive 0.4 mile to Rt. 199.

Pine Plains is said to mark a Pine Grove that served as a Mohican burial ground. State Marker (L).

Turn left on Rt. 199 and drive 6.1 miles to CR 60, Winchell Mt. Rd.

7 UNITED METHODIST CHURCH (L) was established ca. 1835 by Dr. Benjamin Wilber.

8 HARRIS/HUSTED HOUSE (R), ca. 1770 (Marker), a red frame salt box set back from the road is undergoing restoration by the Little Nine Partners Historical Society in Hammertown. This town was the industrial center from the late 1700s to the mid-1900s, boasting the HUSTED TANNERY and HARRIS SCYTHE WORKS. Powered by the Shekomeko Creek, the factory was operated by a noisy trip hammer system that gave the area its name. HAMMERTOWN BARN (L), part of the industrial complex, is now a gift shop.

9 PULVERS CORNERS. Named for William Pulver, this tiny farm hamlet had its own post office, store, hotel and a Union church in the 19th c. It is now distinguished by fine vernacular architecture of the Federal and Victorian eras and lovely views.

Turn left on CR 60, Winchell Mt. Rd. Drive 1.7 miles to Irondale Rd.

10 WINCHELL MT. James Winchell settled here ca. 1760. Marker (R) at turn denotes the “Northeast Pine Plains Line” set in 1823. The Winchell Mt. Cemetery area at the crest commands breathtaking scenic views.

Turn left on Irondale Rd. Drive 0.2 mile to Rt. 22 (Caution).

11 IRONDALE was an early industrial complex devoted to milling and ore processing. Ore beds uncovered north of present day Millerton fed furnaces of the Millerton Iron Co. (1854).

Turn left to Rt. 22. Drive 1.9 miles to CR 62, Rudd Pond Rd. Turn right on Rudd Pond Rd. and drive 3.4 miles to Simmons St., Village of Millerton.

12 RUDD POND. Campsites with showers, beach, boat rentals, children’s play area, cross-country skiing, fishing, and forest land.

Turn right on Simmons St. to Village Hall (R). Drive 0.2 mile to Dutchess Ave. Turn left on Dutchess Ave. Drive 0.1 mile to Main St. Turn right on Main St., then bear left on Main St. and drive 0.2 mile to turn-around at Railroad Plaza.

13 MILLERTON VILLAGE was incorporated in 1875. Park and walk to sites and shops along Main St. Tourist information at GILMOR GLASS, 2 Main St. Settled earlier, as a result of the extension of the NY and Harlem RR planned by Sidney G. Miller, for whom the village is named. The first RR station, erected in 1851, was replaced in 1911 by the present structure, now centerpiece of new commercial development.

Turn left on Main St., drive 0.3 mile to CR 62.

Business landmarks: 1851 FINCH BUILDING (R) (the first commercial building), TERNI’S store 1867, the 1903 BENEDICT HALL (R) (former Grange) theatre/clock tower, now an arts center. Opposite is the MILLERTON METHODIST CHURCH (L) (1858), the oldest church in the village, and the VETERANS’ MEMORIAL (L) (1894). The Victorian style home (ca. 1854) of Edward Simmons, 19th c. educator/entrepreneur, is now SIMMONS’ WAY VILLAGE INN (L).

Turn right at light to CR 62. Drive 1.6 miles to CR 61. Turn right on CR 61, Indian Lake Rd. Drive 0.6 mile to Downey Rd.

The COLEMAN STATION HISTORIC DISTRICT, an intact farmscape reflecting the evolution of community farm practices, includes Colonial revival “Hiddenhurst” and the 1780 Ezra Clark House, both (NR). Roadside farms, like DAISI HILL, feature corn, pumpkins, flowers and seasonal produce.

Turn right on Downey Rd. Drive 1.5 miles to Rt. 22. (stop sign)

14 HARLEM VALLEY RAIL TRAIL (pass under it). Twelve miles of scenic paved walking, rollerblading, biking and cross-country skiing trails from Wassaic to Millerton in Dutchess County. (Caution) at underpass (I) with Mill Rd.

To left of stop sign is NORTHEAST BURYING GROUND, whose earliest stone dates to 1801.

At stop sign turn right on Rt. 22 and drive less than 0.1 mile to CR 64. Turn left on CR 64, McGhee Hill Rd. Drive 3.7 miles to CR 83. Bear right at (I) with Silver Mt. Rd. Follow CR 64 past Scribner Rd. Bear right at Charlie Hill Rd.

15 SILVER MT AND CHARLIE HILL RDS. The crest of this long hill was a favorite spot of FDR. In summer varying shades of green indicate specific crops. In fall the trees are a splash of bright yellows and reds. Dutch Belted cattle and other unusual livestock breeds graze near the road. It offers views, east and west, of sunrise and sunset. The crest on Silver Mountain known as Sunset View was one of FDR’s favorite spots for a picnic.

Turn left at the (Y). Drive 7.9 miles to Rt. 44.Bear left on CR 83 at Separate Rd. into Smithfield hamlet.

16 SHEKOMEKO hamlet, named for the native people of the area, was a 19th c. industrial center of milling and lead and silver mining. Now its major industry is agriculture; its main business the SHEKOMEKO GENERAL STORE (L). DUNROMIN FARMS (L) (PVT) breeds horses. BOCKEE/WHEATON BURIAL GROUND/SQUARE CEMETERY, 1776 (L) marks a 19th c. neighborhood called Federal Square, for a general store of the same name.

17 GREEK REVIVAL SMITHFIELD CHURCH (L), 3rd on the same site since 1750, was built 1847. A great oak that stood across the way in the burying ground until the 1990s was the pulpit for the famous Methodist evangelist George Whitefield, who spoke to hundreds of the faithful here in 1770 at the height of the Great Awakening Revival. Scenic views. White fences and grazing horses identify the hamlet as a center of equestrian related activity. The brick 18th c. main house of former “SMITHFIELD FARMS” is (L) on a hill overlooking pastures.

Turn right on Rt. 44, the old Sharon Turnpike. Drive 1.9 miles to Millbrook School Rd. Turn right on Millbrook School Rd. Drive 1.7 miles to Leavitt Rd.

18 TREVOR ZOO (R) is a favorite destination for many public school elementary classes in the area. It is part of the MILLBROOK SCHOOL, a private co-educational secondary school est. 1931 as a boys’ prep school. The school has been used as background in several major films. CAUTION. Drive slowly. Visitors wishing to tour the campus should check at the Main Building. Call 845/677-3704 for (?).

Turn right on Leavitt Rd. 0.1 mile to CR 86. Turn left on CR 86. Drive 0.8 mile to Pugsley Hill Rd. Turn right on Pugsley Hill Rd. Drive 1.3 miles to entrance to Wethersfield.

19 WETHERSFIELD. The former Chauncey Stillman estate is noted for its gardens, stables and art collection. Call 845/373-8037 for (?).

Turn around and drive 1.3 miles back to CR 86. Bear right on Bangall/Amenia Rd., CR 86. Drive 4.1 miles to CR 65.

This scenic road leads to the hamlet of Bangall. RYDER POND wetlands are home to a variety of wild life and thousands of birds including Canadian geese for which motorists may need to wait at unmarked goose crossings. PRANTLACK FARMS (L) is among a growing number of horse breeders in the county.

20 CAGNEY FARM (R). Scenic views surround a modest stone ranch house, the former home of screen immortal, James Cagney. Caution, steep, curving hill.

Turn left on CR 65. Drive 0.5 mile to Rt. 82. Go straight on Rt. 82.

21 BANGALL. Park near the former RR STATION (L) at (I) of CR 65 and 87. The red frame COUNTRY STORE (R), a 19th c. general store, is now famous for its deli and super special sandwiches. Bangall grew in the late 18th and early 19th c. around a mill and inn/stage stop. It later became a passenger and freight center of the Newburgh, Dutchess and Conn. RR. The Georgian style BULLIS HALL (L), ca. 1815 (NR), a bed and breakfast is at the (Y) opposite the long two-story former inn at the road edge. Other attractions around the small green/VETERAN’S MEMORIAL PARK (L) include shops, the STAGE STOP INN (L), which features Cagney memorabilia, and the 1915 country post office owned by the STANFORD HISTORICAL SOCIETY (R). 500 ft. east on CR 65 toward Hunn’s Lake is the Greek Revival BANGALL METHODIST CHURCH (R) (1843) and picturesque village homes. *(Off route) CR 65 East passes Roseland Ranch, a year round resort. Call 800/431-8292 for (?).

Drive 0.8 mile to CR 19.

22 STANFORDVILLE, a 19th c. commercial/milling hamlet which borders Rt. 82 was a hub of the Poughkeepsie, Hartford and Boston RR. Town government is housed in the former STANFORD UNION FREE SCHOOL (L). Enterprises like the GRANGE (R) chartered 1896, catering to an agricultural community, are in evidence year round, but local produce stands appear in the summer. Bulls Head Rd. on right intersects with Rt. 82 between ca. 1900 vintage frame commercial buildings.

Turn right on Bulls Head Rd. Caution.

The final leg of the tour is a narrow rural lane that passes over the WAPPINGER CREEK (L) at the site of a mill which variously processed grain paper and cotton.

Drive 4.9 miles to Taconic State Parkway.

23 BULLS HEAD/OSWEGO QUAKER MEETING HOUSE (R). Quakers established meetings in Stanford at the end of the 18th c.

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