15 Best Things to Do in Holliston (MA)

In the MetroWest area of Greater Boston, Holliston is a small town with a lot to love about it.

Holliston center is the kind of downtown that instantly wins you over, with businesses that have been here for many years, taking no customer for granted.

Recently, a stretch of railroad abandoned since the 1980s has been converted into a trail, running the whole length of Holliston and passing through downtown.

The local lake, within walking distance of the center, has two beaches with lifeguards on duty in the summer, and the surrounding countryside has farms where you can pick your own fruit, or try yoga with baby goats.

1. Downtown Holliston

It’s difficult not to fall in love with Holliston’s historic core, which continues to be the town’s civic and commercial heart. Later in this list we’ll talk about a few of the businesses that have been a part of the scenery in downtown Holliston for generations.

These await you at the intersection of Central Street and Washington Street, and you should give yourself as much time as possible, hopping from an old-fashioned candy shop to antiques emporium, deli, gift shop, an historic diner, and fashion boutique.

Washington Street here is preserved as the Thomas Hollis Historic District. A lot of the development took place before the Civil War, leaving the district with some excellent examples of Federal, Greek Revival and Italianate architecture.

Check out the Greek Revival/Italianate Town Hall (1855), the Federal style First Congregational Church (1822), and the Federal style Asa Whiting House (1817), now home to the Holliston Historical Society.

2. Lake Winthrop

Go south from Holliston center, and within half a mile you’ll arrive at the north shore of this 131-acre great pond.

In the 17th century, when what is now Holliston was within the territory of a Colonial praying town, the Nipmuc village of Mucksquit was set on the lake’s southwestern shore.

Not only is Lake Winthrop a place of real natural splendor, it’s also easy to access the shore, with public parks on the east and west shore, at Stoddard Park and Pleasure Point respectively.

Both parks have sandy beaches, playgrounds, picnic pavilions and boat launches. Memorial Day weekend through Labor Day, a day pass is required at both beaches, and these could be purchased online or at the gate when we wrote this article.

3. Upper Charles Rail Trail

When we went to press, almost seven miles of this rail trail had been completed in Holliston, from the Milford to Sherborn town lines.

This is on the old Milford Branch of the Boston & Worcester Railroad, dating to the 1840s and passing through downtown Hilliston.

The trail is around ten feet wide and paved with hard-packed stone dust, and includes wonderful pieces of old infrastructure like the Phipps Tunnel.

Where the trail crosses Holliston’s center, there’s a pair of old depot buildings, one housing a pub (Casey’s) and another containing a package store going back to 1959. When completed the Upper Charles Rail Trail will be 24 miles long, linking Framingham with Milford.

4. Holliston Superette

One of downtown Holiston’s long-term mainstays is a deli and butcher shop that first opened in 1960.

Holliston Superette takes pride in its old-fashioned, personalized customer service, and draws a big lunchtime crowd for its hand-crafted sandwiches, made with Boar’s Head cold cuts.

A few faves are hot sandwiches like the chicken parm, porketta, meatball & cheese, and the pastrami & cheese, but the extensive lineup of cold options doesn’t disappoint.

You could visit every day for almost a month and never have the same sandwich twice. There’s a wide variety of other prepared foods, along with deli meats and cheeses, seasonal fruits and vegetables, along with baked goods made fresh daily.

5. Holliston Grill

Open for more than two decades now, the little Holliston Grill is a quintessential American diner, loved for its simple breakfast and lunch dishes, prepared with quality ingredients and served in big portions.

The story of the building goes back much further, and for half a century this spot was known as Pete’s Lunch. You can take a seat in booths along the wall or join in the lively conversation at the counter on one of the vintage stools.

Menu picks include the three-egg omelets (with home fries and toast), the buttermilk pancakes, the corned beef hash (made to a special recipe), and lunch options like grilled cheese and tuna & egg salad.

6. Putts and More

If you’re in need of an idea for a summer family activity, there’s an 18-hole mini golf course along Concord Street in Holliston.

The course at Putts and More resembles an ornamental garden, with its neatly trimmed topiaries, hedges, and shrubs, as well as lawns and water features.

If you consider yourself an accomplished putter in need of a challenge, the holes are a good test of skill, without many crazy obstacles.

Putts and More has a few other attractions designed for young family members, like a splash pad and jumping pillow, while the snack bar serves fast food, cold sodas and ice cream.

7. Fiske’s General Store

One of those old-school businesses you hope to come across in a small town, Fiske’s General Store is several stores in one.

Most remarkable though is its great age, dating back 1863, making it by far the oldest business in the town.

The store lives up to its motto, “Most everything”, stocking craft supplies, children’s toys, home decorations, fashion accessories, Holliston-themed souvenirs, board games, puzzles, greeting cards, sweet treats, and a huge assortment of other items.

8. Happy Goats Farm

If you’ve ever wondered what it’s like to do yoga surrounded by friendly baby goats, you can find out at this farm, less than a mile from downtown Holliston. Happy Goats Farm began raising goats in the 2010s after falling for their playful personalities.

The farm produces raw goat milk, as well as certified organic eggs that you can purchase at a self-serve farmstand. Starting in spring there’s a whole season of outdoor yoga classes with baby goats, which are chaotic and relaxing in equal measure.

Also look out for the annual holiday market in December, with friendly goats wearing reindeer antlers to greet you, and a range of organic handmade gifts for sale.

9. Ashland State Park

On the Holliston/Ashland town line, this state park is on the shore of a former reservoir, built in 1895 and retired just after WWII.

Ashland State Park deserves your attention at any time of year, but especially in summer when you can laze on the beach and enjoy a cookout at the adjoining space.

As well as swimming, Ashland Reservoir is a destination for kayaking, paddleboarding, and fishing, and has little islands that you can paddle out to and explore.

Out of the water, the hiking loop encircling the reservoir is 4.6 miles long and takes you past the 19th-century dam and spillway, listed on the National Register of Historic Places.

10. Vietnam NEMBA Property (Adams Street Conservation Land)

In the southwestern corner of Holliston and crossing the line into Milford and Hopkinton is more than 1,000 acres of publicly accessible land with many miles of single track and double track trails designed for mountain biking.

Enveloped in this landscape is a famous 47-acre parcel that was purchased by the New England Mountain Bike Association in 2003 to prevent it from being developed.

Vietnam is known across the region for its highly technical trails, aimed at intermediate and advanced riders. There’s parking along Adams Street on the Holliston side, and the town’s website has a detailed map to help you navigate the trails and locate the NEMA property.

11. Our Lady of Fatima Shrine

One of the three mission centers in the United States for the Xaverian Missionaries can be found in Holliston. Established in the 1940s, this is in a rural setting, just off the Upper Charles Rail Trail, in the southwest of the town.

On the grounds of the church is a shrine for the claimed Marian apparitions witnessed by shepherd children in Portugal in 1917.

A fascinating detail is the cross section of a Californian sequoia, dating back 3,000 years, accompanied by a plaque pointing out the size of the tree during important events in history.

On December evenings there’s a lovable Christmas light display, which can be enjoyed with some hot cocoa and whipped cream.

12. Patt’s Blueberries

Abutting a large swath of conservation in Holiston’s bucolic countryside, this locally-owned fruit farm welcomes the public during a short window every summer.

Offering pick-your-own blueberries—nothing more and nothing less—Patt’s Blueberries is open Thursday, Friday and Saturday during the picking season, which is usually from around mid to late July.

Depending on the annual conditions the berries can be huge, and it’s not hard to fill the 5 lb coffee cans provided.

The owners have a Facebook page to keep you updated about the season, and you can pick up a recipe card at the far for some cooking inspiration.

13. Goodwill Park

This small public park is on the west side of Holliston’s center, a short walk from local shops and restaurants.

Despite being so close to downtown, Goodwill Park is in a calm residential neighborhood, bounded by woods and a line of houses along Green Street.

On these five acres there’s a baseball/softball diamond, a large field used for soccer, along with pickleball courts and a newly updated playground for kids.

This area is fenced, with a sand box, equipment suited to younger children, and a picnic pavilion next door.

14. Holliston Lions Carnival

For more than 60 years, the Holliston Lions Club has organized a summer carnival in the town. This normally happens at Holliston High School, across four nights in mid-July.

There’s a crowd-pleasing lineup of rides and game booths, as well as a food tent serving fairground bites like burgers, hot dogs, pizza, chili, chicken nuggets and fries.

Admission is free, and you can buy wristbands to give you access to all the rides. The event closes on the Saturday night with a big fireworks show.

15. Old Fashioned Harvest Fair

The Holliston Historical Society is based at the stately Asa Whiting House, built in the Federal style in 1812 and paired with a barn that dates to 1817.

Every September for the last 40+ years, the homey lawn here has hosted a much anticipated antiques and crafts fair.

You can come and spend some time browsing more than 70 vendor booths for a unique hand-crafted item or historic treasure, and there’s much more to hold your interest.

The society hosts an outdoor exhibit of interesting pieces in its collection, and there’s also a silent auction, as well as hot food provided by the society in the historic barn.