15 Best Things to Do in Pepperell (MA)

On the MA/NH line in Middlesex County, Pepperell is a rural town with a diversity of farms where you can pick your own fruit, meet barnyard animals, or simply purchase fabulous fresh produce and pastured meat from farm stands.

The land was first settled in 1720 and Pepperell became a full-fledged town in 1775 at the dawn of the Revolutionary War.

The Nashua River flows through Pepperell, and is crossed by the closest surviving covered bridge to Boston, one of only three to be open to vehicular traffic in Massachusetts.

Pepperell is also renowned for having one of the earliest 4th of July celebrations in the area, with an action-packed parade, evening celebration and fireworks normally falling on the fourth Saturday in June.

1. Pepperell Covered Bridge

Carrying Groton Street across the Nashua River is one of just three covered bridges in Massachusetts to be set on a public road and open to vehicles.

There has been a crossing at this site since around 1740, and a few days after the Battles of Lexington and Concord in 1775 this was the place where a group of local women captured a pair of Loyalists carrying dispatches intended for the British.

The first covered bridge was erected here in the 1840s. This was replaced by the Chester H. Waterous Bridge in 1963, and again by the current structure in 2010.

2. Nashua River Rail Trail

Pepperell is one of five towns on a multi-use rail trail between Ayer, MA and Nashua, NH.

On the Massachusetts side of the boundary, the 12.5-mile Nashua River Trail is maintained by the Department of Conservation and Recreation (DCR), and is open to walkers, cyclists, horseback riders, cross-country skiers and more.

The trail is paved throughout, and is on the railbed of the Worcester & Nashua Railroad (1848) connecting Worcester and Nashua.

Passenger services ended in the 1930s and the line was abandoned in the early 1980s, before being paved as a trail some 20 years later.

The Nashua River Rail Trail is loved for its rural landscapes, passing woods, swamps, ponds, and pastoral farmland, with a lot of opportunities for viewing wildlife.

3. Pepperell Center Historic District

Lawrence Library, Pepperell Center Historic District

The charming old core of the town can be found at the intersection of four main arteries. The town common was laid out here in 1740, and you can still make out the foundation lines of Pepperell’s first church from that time.

The surrounding historic district is dotted with stately 18th-century residences, as well as a former post office building that has been converted into a home.

One of the big landmarks is the Town Hall, built in the Wooden Gothic style at the crossroads in 1874.

Further east along Main Street is the elegant Beaux-Arts Lawrence Library (1901), designed by New York architects Ernest Flagg (1857-1947) and Walter B. Chambers (1866-1945).

4. Heald Pond Conservation Area and Heald Street Orchard

A lot of Pepperell’s rural beauty can be enjoyed up close at a variety of town-owned conservation lands. Arguably the prettiest of these is 30 acres of woods and fields on the shores of the beautiful Heald Pond.

Setting off from the parking area on Heald Street, the trail wraps around the western and southern shores of the pond.

You can also take a detour along Blood Brook Ravine, which shoots out to the west of the pond, or continue round to the east and enter the 80-acre Heald Street Orchard.

Still growing apples, the latter was once a working orchard that has returned to nature. You’re permitted to pick apples here in season, while the orchard provides a habitat for numerous bird species, including ospreys, savannah sparrows, blue-winged warblers and chimney swifts.

5. Skydive Pepperell

Operating out of a private airport on the MA/NH border, Skydive Pepperell is officially the closest skydiving dropzone to Boston.

With fully licensed and certified instructors, this company is a member of the United States Parachute Association (USPA) and the Parachute Industry Association (PIA).

Skydive Pepperell is a hub for a community of experienced skydiving, and runs an Accelerated Freefall Program for people who want to gain their skydiving license.

If you’re a first-timer you can always opt for a tandem jump, experiencing the rush of freefalling at 120 mph and sensational views of New England, while safely attached to an instructor.

6. Kimball Fruit Farm

On the MA/NH line in the north of Pepperell there’s a fruit farm that has been worked by the same family for more than half a century.

Kimball Fruit Farm is on land that has been used for agriculture for more than 300 years—the panoramic hilltop picnic area here is on the filled-in foundation of the original Colonial house and barn.

From mid-June to October, you can visit the farm to pick your own produce, including strawberries, raspberries, blueberries, flowers, blackberries, apples and pumpkins.

There’s a harvest schedule on the farm’s website, while the farm stand is beloved for its heirloom tomatoes, peaches, apple cider donuts and pies.

7. Nissitissit Meadows Conservation Area

The north of Pepperell is a fantastic place to go for a hike in nature, as there’s a series of town-owned conservation properties, adjoining Massachusetts Fisheries and Wildlife land.

An ideal starting point for a walk here is the Nissitissit Meadows Conservation Area, with more than 60 acres of floodplain and river frontage.

Your journey here will bring you over undulating agricultural fields and through wooded wetlands, with ponds and stretches of riverfront.

Birdhouses have been set up in the meadows and wetlands, and this is a fine place to spot sparrows, bluebirds, eastern meadowlarks, bobolinks and hawks in season.

8. Dr. Davis Ice Cream Stand

This ice cream stand at 67 Hollis Street in Pepperell goes all the way back to 1939. If you’re curious about the name, Dr. Davis was a local veterinarian who specialized in treating farm animals.

He was also known for putting on summer entertainment for the locals in Pepperell, hosting live concerts or even projecting movies onto the side of his house.

The ice cream he served on these occasions was as popular as the entertainment, so he decided to go into business.

Dr. Davis Ice Cream Stand has changed owners a couple of times since then, but remains a local institution serving its own ice cream.

The famous Doc’s Special here is two scoops of ice cream, sliced banana, hot fudge, strawberries, and marshmallow or whip cream.

9. Nashua River Westside Trail (Brookline and Milford Branch Railbed)

On the west bank of the Nashua River there’s another stretch of abandoned railbed, about a mile of which was purchased by the town for conservation in 2002.

This is a gorgeous walk, set close to the river bank through lush woodlands, and past several ponds.

There are no plans to pave the railbed, as it offers a wilder alternative to the Nashua River Rail Trail on the opposite bank.

You can pick up the trail along Route 119 near the Wilkins Farm Stand, and can travel north as far as Kemp’s horse track, with a couple of other sections accessible further north in Pepperell.

The line was part of the Boston & Maine Railroad, constructed in the late 19th century to provide a route between Ayer, MA and Milford, NH, but abandoned in the 1930s.

10. Wilkins Farm Stand

At the intersection of Shirley Street and South Road, the family-run Wilkins Farm was founded by Russell Wilkins in the late 1940s, and has been a source for superb fruits and vegetables for decades.

During the season the quaint farm stand has everything from cherries to apples, pumpkins, tomatoes, corn, peaches, strawberries, greens, garlic, cucumbers, peppers, and a whole lot more.

As well as super fresh produce, the farm stand has fresh baked pies, fudge, and homemade brownies, along with cut flowers, eggs, honey, syrup, preserves and a range of local frozen meats.

11. Luina Greine Farm

A little way south in Groton there’s a family-owned alpaca farm on 20 rolling acres. Luina Greine Farm was established in 2011, and opens to the public on weekends during the fall season (mid-September through December).

On these days you’ll be given a free tour of the property, including the idyllic apple orchards, and will get to meet the farm’s animals.

You can feed the friendly alpacas, hang out with the Nigerian dwarf goats, hold an Indian runner duck, and pet and feed a miniature donkey. The farm store is filled with alpaca wool products, from scarves to socks, hats, coats and plush toys.

12. Clover Luck Farm Dairy

For another agritourism experience there’s a picturesque dairy farm in the west of Pepperell near Heald Pond. Clover Luck Farm has a herd of Normande and Jersey cows producing high-quality raw milk and superb cheeses.

You can also purchase free range eggs, and a variety of meats including pastured pork and grass-fed beef.

The farm store is open during normal business hours, seven days a week, and the owners are always keen to show off the farm to the public.

The facility is clean and the livestock are healthy and well cared for, and the children will enjoy seeing the cows in the fields.

13. Franny’s Diner

Previously known as Breen’s Diner, this spot opened downtown at 170 Main Street in 2014. Inside, you could be forgiven for thinking Franny’s Diner was much older.

There’s a nostalgic 50s theme, with a checkered floor, a soda fountain, a counter with stools, a jukebox with 50s hits, vintage memorabilia on the walls, and a row of booths with leatherette seating.

Breakfast is served all day, and one of the standout menu items is the eggs benedict. Like most of the menu these are served with homefries, which are extremely popular here. Also check out the omelets, the chicken & waffles, and, for lunch, the Cuban sandwich.

14. Fourth of July Parade

4th of July Celebration Fireworks — 4th Of July Celebration Fireworks

A hotly anticipated spectacle in late June is the wonderful procession of fire trucks, floats, marching bands, vintage vehicles, dancers, and more, making their way along Peperell’s Main Street to mark the nation’s independence.

Usually running from the town hall to Railroad Square, the Fourth of July Parade features a wealth of local clubs, services, and other organizations, but individuals are also welcome to enter their own floats.

The parade has been held for more than three decades now, and is followed by a celebration in the evening, and fireworks on the Town Field.

15. Pepperell Fall Fest

The committee planning Pepperell’s Fourth of July celebrations is also responsible for this successful event in mid-September at Pepperell Town Field.

Pepperell Fall Fest is attended by thousands of people, featuring more than 100+ booths for local crafters, and a range of other businesses and organizations.

The festival features a diversity of food trucks (BBQ, burgers, pizza and more), contests, plenty of live entertainment, and tons of things for wee ones to get up to, including pony rides, hayrides, a petting zoo, face painting, inflatables, and games.