15 Best Things to Do in Pepperell (MA)

On the MA/NH line in Middlesex County, Pepperell is a rural town with a variety of farms where you can pick your own fruit, meet barnyard animals, or purchase great fresh produce and pasture-raised meats at the farm stand.

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

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

Pepperell is also known for one of the region's oldest Fourth of July celebrations, with an action-packed parade, evening festivities and fireworks typically held on the fourth Saturday in June.

1. Pepperell Covered Bridge

Carrying Groton Street across the Nashua River, it is one of only three covered bridges in Massachusetts that lie over a public street and are open to vehicles.

There has been a crossing at the site since about 1740, and in 1775, days after the Battles of Lexington and Concord, this was where a group of local women captured a pair of Loyalists who were being sent to the British.

The first covered bridge was built here in the 1840s. It was replaced by the Chester H. Waters Bridge in 1963, and then by the current structure in 2010.

2. Nashua River Rail Trail

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

On the Massachusetts border, the 12.5-mile Nashua River Trail is maintained by the Department of Conservation and Recreation (DCR) and is open to walkers, bikers, equestrians, cross-country skiers and others.

The trail is completely paved, and is located on the tracks of the Worcester and Nashua Railroad (1848) connecting Worcester and Nashua.

Passenger service ended in the 1930s, and the line was abandoned in the early 1980s, before being paved as track 20 years later.

The Nashua River Rail Trail is known for its rural scenery that winds through forests, swamps, ponds and pasture fields, with many wildlife viewing opportunities.

3. Pepperell Center Historic District

The charming old center of the city can be found at the intersection of four major arteries. The town commons were laid out here in 1740, and you can still make out the foundations of Pepperell's first church from that time.

The surrounding historic area consists of stately residences dating back to the 18th century, as well as a former post office building converted into a house.

One of the main landmarks is the City Hall, built in 1874 in the wooden Gothic style at the intersection.

To the east along Main Street is the Lawrence Fine Arts 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

Much of Pepperell's rural beauty can be enjoyed up close on several city-owned conservation lands. The most beautiful is 30 acres of woodland and fields on the shores of beautiful Loch Held.

Leaving the Heald Street parking area, the trail skirts the western and southern shores of the pond.

You can also turn along Bloodbrook Ravine, which exits on the west side of the pond, or turn east into the 80-acre Heald Street Orchard.

Apples still grow, the latter once a working orchard returned to nature. You're allowed to pick apples here in season, while the orchard provides a habitat for a number of bird species, including osprey, savannah sparrows, blue-winged warblers and smokebirds.

5. Skydive Pepperell

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

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

Skydive Pepperell is a hub for the experienced skydiving community, and runs the Accelerated Freefall program for those looking to obtain a skydiving license.

If you're a first-timer, you can always opt for a tandem jump, free-falling at 120 mph and enjoying the stunning New England scenery while safely strapped to a trainer.

6. Kimball Fruit Farm

North of Pepperell on the MA/NH line is a fruit farm that has been run by the same family for more than half a century.

Kimball Fruit Farm is located on land that has been used for farming for over 300 years, and a beautiful hillside picnic area is located on grounds filled with an original colonial home and barn.

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

The farm's website has a harvest schedule, while the farm stand is popular for its tomatoes, peaches, apple cakes and pies.

7. Nissitissit Meadows Conservation Area

North Pepperell is a great place to take a nature hike, with a series of city-owned, protected properties adjacent to Massachusetts Fisheries and Wildlife lands.

An ideal starting point for hiking here is the Nissitissit Meadows Conservation Area, which includes more than 60 acres of floodplain and river frontage.

Your journey here will take you through undisturbed agricultural fields, forested wetlands, ponds and riverbanks.

The birdhouses are located in grasslands and wetlands, and in season it is a good place to see sparrows, bluebirds, eastern meadowlarks, bobolinks and hawks.

8. Dr. Davis ice cream stand

Located at 67 Hollis Street in Pepperell, this ice cream shop dates back to 1939. If you're wondering about the name, Dr. Davis was a local veterinarian who specialized in treating farm animals.

He was also known to entertain locals in Pepperell during the summer, hosting live concerts or showing movies around his home.

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

Dr.'s store has changed owners. Davis Ice Cream Stand has opened several times since then, but has remained a local institution that serves its own ice cream.

The famous dock special here is two scoops of ice cream, banana slices, hot fudge, strawberries, marshmallows or whipped cream.

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

On the west bank of the Nashua River is another stretch of abandoned railway, about a mile of which the city purchased for preservation in 2002.

It is a beautiful walk, passing through lush green forests and several ponds along the river banks.

There are no plans to pave the railway, as it provides a land 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 travel north to the campground's horse trail, which has a few more accessible sections north on Pepperell.

The line was part of the Boston and Maine Railroad, built in the late 19th century to provide a route between Ayr, Massachusetts and Milford, New Hampshire, but was 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 of premium fruits and vegetables for decades.

In season, the single farm stand has everything from cherries to apples, squash, tomatoes, corn, peaches, strawberries, greens, garlic, cucumbers, peppers and more.

In addition to ultra-fresh produce, the farm stand features an array of freshly baked pies, candy and homemade cakes as well as fresh cut flowers, eggs, honey, juices, preserves and local frozen meats.

11. Luina Greine Farm

A little south in Groton is a 20-acre family-owned alpaca farm. Founded in 2011, Luina Greine Farm is open to the public on weekends during the fall season (mid-September to December).

On these days, you will be given a free tour of the property, including the beautiful apple orchards, and will have the opportunity to meet the farm animals.

You can feed cute alpacas, hang out with Nigerian dwarf goats, hold Indian ducks, pet and feed baby donkeys. The farm shop is full of alpaca wool products, from scarves to socks, hats, coats and plush toys.

12. Clover Luck Farm Dairy

For another agritourism experience, west of Pepperell is a charming dairy farm near Heald Pond. Clover Luck Farm has a herd of Normandy and Jersey cows that produce high-quality raw milk and excellent cheese.

You can also buy free-range eggs and a variety of meats, including pasture-raised pork and grass-fed beef.

The farm store is open during regular business hours, seven days a week, and the owners are always willing to showcase the farm to the public.

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

13. Franny’s Diner

Formerly known as Breen’s Diner, the location opened in 2014 downtown at 170 Main Street. Inside, you could be forgiven for thinking Franny’s Diner is very old.

There's a vintage '50s feel, with checkered floors, a soda fountain, a counter with stools, a jukebox with songs from the '50s, vintage memorabilia on the walls, and a row of booths with leather seating.

Breakfast is served all day, and one of the signature menu items is Eggs Benedict. Like most of the menu it is served with home fries, which are very popular here. Also look for omelettes, chicken and waffles, and Cuban sandwiches for lunch.

14. Fourth of July Parade

The most anticipated spectacle of late June is the spectacular procession of fire engines, floats, bands, vintage vehicles, dancers and more, which makes its way along Peperell's main street in celebration of the country's independence.

The Fourth of July parade typically runs from City Hall to Railroad Square, and features a wide array of other local clubs, services and organizations, but individuals are also welcome to enter their own floats.

The parade has now been held for more than three decades, followed by an evening celebration with fireworks in the city square.

15. Pepperell Fall Festival

Pepperell's Fourth of July Celebration Planning Committee is also responsible for this successful event at Pepperell Town Field in mid-September.

Thousands of people attend Pepperell Fall Fest, which features more than 100 booths of local crafts, businesses and other organizations.

The festival features a variety of food trucks (barbecue, burgers, pizza, and more), contests, plenty of live entertainment, and plenty of things for the little ones, including pony rides, horse racing, a petting zoo, face painting, inflatables, and arcade games. .