10 Best Things to Do in Holliston (MA)

Holliston, a small yet charming town in the MetroWest area of Greater Boston, offers a mix of historical charm, outdoor recreation, and unique local businesses. Whether you’re a resident or a visitor, there’s plenty to explore and enjoy. Here’s a closer look at what makes Holliston a delightful place to spend time.

Exploring Downtown Holliston

THE 10 BEST Places to Visit in Holliston (UPDATED 2024)

Holliston’s downtown area is the heart of the town, known for its historic architecture and vibrant community atmosphere. The intersection of Central Street and Washington Street is a bustling hub, home to businesses that have been serving the community for generations. As you stroll through the Thomas Hollis Historic District, you’ll encounter a variety of establishments, from old-fashioned candy shops and antique emporiums to fashion boutiques and historic diners.

Notable buildings include the Greek Revival/Italianate Town Hall, built in 1855, the Federal-style First Congregational Church from 1822, and the Federal-style Asa Whiting House, dating back to 1817, which now houses the Holliston Historical Society. These structures provide a glimpse into the town’s architectural heritage, largely influenced by pre-Civil War development.

Enjoying Lake Winthrop

Pearrygin Lake Family Photos | Reflected Light Images

Just half a mile south of Holliston’s center, Lake Winthrop offers a serene natural escape. This 131-acre lake, steeped in history, once bordered the Nipmuc village of Mucksquit in the 17th century. Today, the lake’s shores are accessible via public parks such as Stoddard Park and Pleasure Point. Both parks boast sandy beaches, playgrounds, picnic pavilions, and boat launches, making them ideal spots for family outings. During the summer months, lifeguards are on duty, ensuring a safe environment for swimming.

The Upper Charles Rail Trail

New England fine art photography that captures the colors, essence and  pulse. | Juergen Roth

The Upper Charles Rail Trail is a favorite among locals and visitors alike, offering a scenic route through the town’s natural beauty. Stretching nearly seven miles within Holliston, this trail is set on the former Milford Branch of the Boston & Worcester Railroad. The path, paved with hard-packed stone dust, is about ten feet wide and passes through Holliston’s center, offering a perfect spot for walking, jogging, or biking.

Along the trail, you’ll find historical remnants like the Phipps Tunnel and old depot buildings. One such depot is now Casey’s Pub, while another houses a longstanding package store. The trail is part of a larger project that will eventually connect Framingham to Milford, spanning a total of 24 miles.

Holliston Superette: A Local Favorite

Contact - Holliston Superette

For a taste of Holliston’s local flavor, the Holliston Superette is a must-visit. This deli and butcher shop has been a mainstay in downtown Holliston since 1960, known for its personalized customer service and handcrafted sandwiches made with Boar’s Head cold cuts. With a wide variety of both hot and cold sandwich options, including favorites like chicken parm and pastrami & cheese, this spot attracts a big lunchtime crowd. In addition to sandwiches, the Superette offers an array of prepared foods, deli meats, cheeses, seasonal fruits, and freshly baked goods.

Holliston Grill: A Classic American Diner

Phillips Avenue Diner | Travel South Dakota

Another beloved dining spot is the Holliston Grill, a quintessential American diner that has been serving hearty breakfast and lunch dishes for over two decades. Set in a building that was formerly known as Pete’s Lunch, the Holliston Grill offers a warm, nostalgic atmosphere with its vintage stools and cozy booths. Popular menu items include three-egg omelets, buttermilk pancakes, and corned beef hash, along with lunch staples like grilled cheese and tuna salad.

Family Fun at Putts and More

Putt-Putt Your Way to Casual Fun at Ryze Adventure Park | RYZE Adventure  Park

For family-friendly entertainment, Putts and More offers an 18-hole mini-golf course designed to resemble an ornamental garden. With neatly trimmed hedges, topiaries, and water features, the course is both aesthetically pleasing and a fun challenge for mini-golf enthusiasts. In addition to mini-golf, Putts and More features a splash pad and a jumping pillow for children, as well as a snack bar serving classic treats like ice cream and cold sodas.

Fiske’s General Store: A Step Back in Time

Fiske's General Store conquers e-commerce competition, pandemic

Fiske’s General Store is a cherished institution in Holliston, having served the community since 1863. True to its motto, “Most everything,” Fiske’s stocks a wide array of items, from craft supplies and toys to home decorations, fashion accessories, and Holliston-themed souvenirs. The store’s old-fashioned charm and diverse offerings make it a must-visit for anyone exploring downtown Holliston.

Yoga with Baby Goats at Happy Goats Farm

Getting Centered with Goat Yoga at Lost Peacock Creamery - ThurstonTalk

A unique experience awaits at Happy Goats Farm, where you can practice yoga surrounded by playful baby goats. Located just a short distance from downtown, the farm began raising goats in the 2010s and has since become a popular spot for goat yoga, particularly in the spring and summer months. The farm also offers organic eggs and raw goat milk for sale, and hosts an annual holiday market in December, where visitors can meet goats dressed in festive attire.

Outdoor Adventures at Ashland State Park

Ashland State Park in 156 W Union St, Ashland, MA 01721, USA

Located on the border of Holliston and Ashland, Ashland State Park is a scenic area centered around a former reservoir. Perfect for year-round recreation, the park features a beach for swimming, areas for kayaking and paddleboarding, and fishing opportunities. A 4.6-mile hiking loop around the reservoir allows visitors to explore the park’s natural beauty, passing historical features such as the 19th-century dam and spillway.

Mountain Biking at Vietnam NEMBA Property

Dang.....Vietnam worked me over today | Mountain Bike Reviews Forum

Mountain biking enthusiasts will find plenty to love at the Vietnam NEMBA Property, a 1,000-acre expanse of land that stretches into neighboring Milford and Hopkinton. Known for its challenging trails, this area attracts bikers from across the region. The New England Mountain Bike Association acquired a 47-acre parcel of this land in 2003 to preserve it from development, ensuring that the trails remain accessible for intermediate and advanced riders.

Holliston’s blend of historic charm, natural beauty, and unique local businesses makes it a delightful destination for visitors and residents alike. Whether you’re exploring the historic downtown, enjoying a day by the lake, or hitting the trails, Holliston offers something for everyone.

FAQs:

What are some popular activities in Holliston?

Holliston offers a variety of activities, including exploring historic downtown, enjoying outdoor recreation at Lake Winthrop and Ashland State Park, hiking or biking along the Upper Charles Rail Trail, and engaging in unique experiences like goat yoga at Happy Goats Farm.

Where can I find historical architecture in Holliston?

The Thomas Hollis Historic District in downtown Holliston is home to several historic buildings, including the Greek Revival/Italianate Town Hall, the Federal-style First Congregational Church, and the Asa Whiting House.

Is there a place for families to enjoy in Holliston?

Putts and More is a family-friendly destination offering mini-golf, a splash pad, a jumping pillow, and a snack bar, making it a perfect spot for summer fun.

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