Sparsely populated and with a rich colonial history, Sudbury is an affluent town in Greater Boston’s MetroWest region.
The United States’ oldest continuously operating inn awaits you in Sudbury, and starting in the 1920s this was the centerpiece for a proposed living history museum by car manufacturer Henry Ford (1863-1947).
His plans never came to fruition, but there are interesting holdovers on the grounds of the Wayside Inn, and further along the Boston Post Road (Route 20) in Marlborough.
In keeping with its rural character, Sudbury has two national wildlife refuges within its limits, as well as a delightful historic center where minutemen rallied before setting off to fight at the Battles of Lexington and Concord at the dawn of the American Revolutionary War.
1. Wayside Inn Historic District
Built in 1686, and in business since 1716, the Wayside Inn is the oldest continuously operating inn in the country.
In 1923 this place caught the imagination of Henry Ford, who tried to create a living history attraction on the property, as a forerunner to his Greenfield Village.
Among the buildings that cropped up are a grist mill, the non-denominational Martha-Mary Chapel and the historically significant Redstone Schoolhouse, relocated from Sterling, MA.
Inside the inn are several museum rooms with colonial-era artifacts, while the emblematic space here is the Longfellow Parlor, which inspired Henry Wadsworth Longfellow’s (1807-1882) collection of poems, Tales of a Wayside Inn (1863).
2. Wayside Inn Grist Mill
One of the must-see attractions on the grounds of the Wayside Inn is the working water-powered grist mill, built by Henry Ford in the late 1920s.
The millpond driving the water wheel goes back to the early 18th century, and the current mill was constructed close to the site of the original Howe family grist mill from that time.
Open to the public, the mill is a picture-perfect slice of rural New England, and once produced flour for Pepperidge Farms, later inspiring the logo for their baked goods.
You can purchase sacks of flour at the inn’s store, and check out milling demonstrations on weekends during busier periods.
3. Assabet River National Wildlife Refuge
A large chunk of western Sudbury is taken up by this 2,300-acre National Wildlife Refuge, on land that was used by the US Army from 1942 until it was handed over to the U.S. Fish & Wildlife Service in 2000.
Along 15 miles of trails you’ll encounter curious vestiges from that past life, in the form of WWII-era ammunition bunkers hiding in the woods.
From the main parking lot in Sudbury you can get onto that large trail network leading through forest and open fields to vernal pools and the shores of the expansive Puffer Pond.
The visitor center is also within Sudbury limits, in a 5,000-square-foot eco-friendly building, with exhibits on the region’s ecology, prehistory and the nation’s pioneering conservationists going back to the 19th century.
4. Sudbury Center Historic District
The historic core of Sudbury is akin to an outdoor museum, with centuries-old architecture around a common, and with stately residences in every direction beyond.
The militia and minutemen mustered at this very place on the morning of April 19, 1775 to fight at the Battles of Lexington and Concord.
Right on the green is the First Parish Church (1797), significant as the focus of the Sudbury Inhabitants vs. Thomas Stearns (1838) suit, determining that the parish, not the town, controlled church records.
To the east is the Greek Revival Town Hall (1846, rebuilt 1932), and Loring Parsonage (c. 1730), now home to the local historical society museum, and on the south side stands the Hosmer House (1793) in the Federal style. There’s a lovely little park here, with a playground and a pond.
5. Sudbury History Center and Museum
In 2021 the Sudbury Historical Society opened a new headquarters and museum at an historic site in Sudbury Center.
This is the Loring Parsonage, built around 1730 as the home of the town’s first minister, and then serving as the residence for a long line of Wheeler and Hayes family descendants.
The exhibit space inside is the Jonathan Baggott Gallery, charting Sudbury’s history in detail from the earliest settlements to the modern day.
Additional galleries go into depth on Rev. Israel Loring and his family, and display selected artifacts from the society’s large archives. The gift shop also deserves your attention, abounding with locally made crafts, clothing and accessories.
6. Tippling Rock
Rising in the south of Sudbury is a prominent outcropping that can be accessed via conservation land that was acquired by the town in the late 1990s.
The summit of Tippling Rock, part of Nobscot Hill, is more than 600 feet above sea level, making it the highest point in the town, with distant views towards Boston.
According to tradition, the boulder atop the outcropping once wobbled back and forth (hence the name), and was used by Native Americans for communication.
From the top you can survey the western suburbs, and spot landmarks like Great Blue Hill, John Hancock Tower, Prudential Building, and Four Seasons Boston.
7. Great Meadows National Wildlife Refuge
The headquarters for the Great Meadows National Wildlife Refuge are located in Sudbury at a unit comprising wildlife-rich freshwater wetlands on the Sudbury River.
Famed for its birdwatching opportunities, this is one of two units adding up to more than 3,800 acres of key wildlife habitat in Sudbury and Concord.
The Sudbury portion features the Weir Hill Trail, for a walk that takes in woods, marshes, the riverside, a brook and pond.
The shorter Red Maple Trail has an observation platform where you can spot marsh wrens, muskrats and painted turtles in the riparian zone. On the water, you can launch a canoe or kayak at the refuge to paddle the 1.5-mile Sudbury River Paddle Trail.
8. Redstone Schoolhouse
Another of the old buildings that make up the Wayside Inn Historic District is this one-room schoolhouse, within a few steps of the Martha-Mary Chapel.
Built in the late 18th century the Redstone Schoolhouse was originally on Redstone Hill in Sterling, MA, and was relocated to the Wayside Inn by Ford in 1927.
According to popular belief in the late 19th and early 20th century, this is the school where Sarah Josepha Hale’s (1788-1879) “Mary Had a Little Lamb” nursery rhyme took place.
This was all based on the recollection of one Sterling resident, Mary Tyler (1806-1889) at the age of 70, who claimed to be the Mary who brought her pet lamb to school one day as a child.
9. New England Garden Company
In Sudbury you can visit the exquisite outdoor display garden and indoor showroom for this company specializing in decorative garden elements.
The largest business of its kind in the Northeast, the New England Garden Company curates an extraordinary array of ornamentation, antique furniture, art, repurposed architectural elements and more, from across America and several countries in Europe.
At this 6,000-square-foot you could lose all sense of time, perusing centuries old finials, stone troughs, sundials, millstones, statuary, fountains, cisterns, Victorian ironwork, the list goes on.
10. Wayside Country Store
Go a little further east along Route 20, and in Marlborough you’ll be greeted by an historic building that until the late 1920s used to stand proud in Sudbury Center.
This is the Wayside Country Store, a vast old-timey candy store, part of Ford’s grand plans for the Wayside Inn.
The Federal-style building used to be known as the Parmenter-Garfield General Store, built in 1790 and serving a few different roles, including a post office and school where future 20th president James A. Garfield (1831-1881) worked as a teacher for a time.
Ford purchased the building in 1928 and sawed it in half before moving it to the north shore of Hager’s Pond on Route 20.
There’s a selection of board games and jigsaw puzzles on the second floor, while the complex also features a European-style bakery and a full-service restaurant.
11. Haskell Field
The local place to go for active recreation, Haskell Field has a ton of sports amenities used for local programs like Sudbury Youth Soccer.
Packed onto this open green space are six small and three large soccer fields, lacrosse fields and a 90-foot baseball diamond.
But the highlight for parents has to be the wonderful playground, which is fenced and has ample space for children aged 2-5 and 5-12 to be active on climbing equipment, swings, slides and shaded picnic tables.
You’ll find restrooms here, as well as a concession stand for cold drinks and snacks.
12. Bruce Freeman Rail Trail
By the time you read this article, Sudbury might be a dream location for hikers and bicyclists, at the intersection of two long-distance rail trails.
The first of these is the Bruce Freeman Rail Trail, which will eventually be 25 miles long, and was under construction in Sudbury when we wrote this list.
This will run for 5.9 miles north to south through the town on the right-of-way of the old Framingham and Lowell Line (1871) of the New York, New Haven and Hartford Railroad.
That trail will connect with the Mass Central Rail Trail, which is on the inactive Massachusetts Bay Transportation Authority Right-of-Way, already a popular but unpaved hiking route in the town.
When complete, the Mass Central Rail Trail will be a 104-mile east-to-west route between Boston and Northampton.
13. Duck Soup
In that long list of worthwhile stops along Route 20 is this mom and pop store, with a diverse range including everything from gourmet foods to high-end kitchenware, handmade ceramics and locally produced spirits.
Supporting local and regional makers, Duck Soup has been open for more than 50 years now, and made headlines in 2018 when it acquired the right to manufacture the beloved Sky Bar, a candy introduced in 1938 by Revere’s now defunct Necco company. This is made and sold at a separate storefront, just next door.
In the main store you can browse a wealth of specialty products made in New England, from rum to maple syrup, as well as an endless choice of candy and snacks imported from as far afield as the UK, South Africa and the Netherlands.
14. Garden in the Woods
Just across the line in Framingham there’s a sensational botanical garden, hiding in mature oak forest and serving as the headquarters of the Native Plant Trust.
Open from mid-April to mid-October, the Garden in the Woods is dedicated to native New England species, boasting the largest landscaped collection of wildflowers in the region, with some 1,700 plants from 1,000 species, many of which are rare or endangered.
Across 30 years, the garden was the pet project of landscape designer Will C. Curtis (1883-1969) and was deeded to the New England Wild Flower Society on his death. Also important here is New England’s largest retail native plant nursery.
15. Boston Paintball Maynard
On the Sudbury/Maynard line there’s an outdoor paintball facility open seasonally April through November.
With a mix of wooded and open environments, these three courses are on the grounds of the Maynard Rod and Gun Club.
Most memorable is the Maynard Outpost, a thrilling building-to-building field, with several multilevel structures and interesting obstacles like destroyed tanks.
The woodsball field, known as Bunker Hill, has several huts and towers and a downed helicopter, below a towering hill that offers a big strategic advantage. Walk-on play is available on weekends, and reservations are required on weekdays.