15 Best Things to Do in Milford (MA)

Written by Jan Meeuwesen
Updated on
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An historic manufacturing center in the Blackstone Valley, Milford is renowned for its pink granite, discovered in 1870 and quarried for buildings like the Boston Public Library (1895) and Worcester City Hall (1898).

Milford is near the source of the famous Charles River, and there’s a growing rail trail along the CSX right-of-way, tracking the streams and ponds that make up the river’s headwaters.

With a proud hardscrabble character, Milford Center is a tight-knit, home to homey, old-school taverns, beautiful 19th-century architecture and lots of local shops.

One of just three remaining drive-in theaters in Massachusetts is within a couple of miles of Milford, and one of the top mountain biking areas in New England is in the town’s backyard.

1. Upper Charles Trail

Upper Charles TrailSource: Yingna Cai / shutterstock
Upper Charles Trail

If everything goes to plan this rail trail will soon spread across several towns, including Ashland, Sherborn, Holliston and Hopkinton, all along abandoned CSX rail beds.

Milford has a head start on its neighbors with more than 6.5 miles of trails already completed. You can get on the Upper Charles Trail in the town center, and walk or ride north to the line with Hopkinton, east to Holliston, and south as far as the Milford Senior Center.

Heading north to Hopkinton, the trail follows the headwaters of the Charles River, weaving between Milford Pond and Louisa Lake and crossing the stream a few times.

2. Memorial Hall

Milford Memorial HallSource: Yingna Cai / shutterstock
Milford Memorial Hall

One landmark that will hold your attention in Milford Center is the Romanesque Revival Memorial Hall (1884), which was built to commemorate the Civil War.

This was designed by local architect Frederick Swasey and is composed of Milford granite, with Longmeadow brownstone for its cornice, windows and large main portal.

You can go inside on Thursday afternoons to browse the museum run by the Milford Historical Commission.

This shines for its exceptional display of Civil War artifacts and musical instruments, as well as a trove of memorabilia covering many facets of local history.

3. NEMBA Trails at Milford (Vietnam)

NEMBA Trails at MilfordSource: MYSTERY PILL / Flickr | CC BY
NEMBA Trails at Milford

In 2003 the New England Mountain Bike Association (NEMBA) took the unprecedented step of purchasing almost 50 acres of land on the line between Milford and Holliston.

This was done to preserve a popular tangle of trails that had long been known as “Vietnam”, connecting parcels of conservation land in both towns (as well as the Upper Charles Bike Trail), adding up to some 1,000 acres of open space.

You could ride for hours through the rock-strewn woods, across brooks and next to ponds, without seeing the same scenery twice. And that’s not just because these trails are highly technical and will require most of your concentration.

4. Main Street Milford

Gillon Block, Main Street MilfordSource: Yingna Cai / shutterstock
Gillon Block, Main Street Milford

Crossed by the Upper Charles Trail in the north, Milford’s main commercial area is hopping with small businesses, and has an attractive little green in the south at the Draper Memorial Park.

As well as a clutch of traditional taverns, there’s a Brazilian flavor along Main Street, with several restaurants, a bakery and stores aimed at Brazilian residents.

On the main drag you’ll happen upon plenty of other locally owned shops, specializing in musical instruments, home brewing supplies, clothing, crafts, jewelry and more besides.

To go with Memorial Hall, a fine building downtown is the Town Hall at No. 52, built in the Italianate style in 1854, and placed on the National Register of Historic Places in 1977.

At 189 Main Street, check out the four-story Gillon Block (1888), with intricate brickwork on its facade.

5. CraftRoots Brewing

CraftRoots BrewingSource: CraftRoots Brewing / Facebook
CraftRoots Brewing

Milford’s first ever brewery was born in 2014 when this craft brewery opened in an industrial park on the east side of town.

On top of that, the 7-barrel CraftRoots Brewing has the distinction of being the first 100% woman-owned brewery in all of Massachusetts.

The taproom, with its 24-foot bar, has a clear view of the tanks, and is a venue for live music on weekends. The flagship beers are a Blonde Ale, Irish Dry Stout and a pair of NEIPAs, with Sours and an Irish Red Ale among the rotating drafts.

There’s no kitchen, but food trucks come by on weekends, for wings, lobster rolls, empanadas, Caribbean food and more.

6. Depot St Tavern

Depot St TavernSource: Depot St. Tavern / Facebook
Depot St Tavern

CraftRoots Brewing is one of a long list of regional craft beer suppliers to this much-loved local tavern, set just east of Milford Center.

In the same vein, Depot St Tavern sources many of the ingredients for its kitchen from the area, while the interior has a relaxed and homey feel, with its decor of vintage street signs and license plates.

The building is the former Crivillo’s Crossing diner, open from 1938 to 2013, and the tavern became an almost instant success when it opened in 2014, with lines out the door weekends.

Food-wise the menu is pub grub favorites like fish & chips, baked mac & cheese, chicken parmesan, and a selection of paninis, burgers and subs. Come with an appetite early in the day and there’s a lineup of omelets, benedicts, waffles and pancakes.

7. Peppercorn Hill Conservation Area

BinocularSource: PanyaStudio / shutterstock

On the town line with Milford, this 283-acre swath of rugged woodland is managed by the Upton Conservation Commission.

There’s a surprising array of habitats at the Peppercorn Hill Conservation, with pine, oak and maple woods, and vernal pools, streams and wetlands.

The main loop is around 2.5 miles long and brings you to a spectacular overlook. There are stone walls throughout, and the western slope of Peppercorn Hill is scattered with glacial erratics, boulders deposited here at the end of the last Ice Age more than 10,000 years ago.

8. PiNZ Bowl Milford

BowlingSource: Aleksandar Karanov / shutterstock

This family entertainment center combines a few attractions in one large complex. The main alley area has 16 lanes with state-of-the-art scoring, food and beverage service, and a surround entertainment system with a special light display.

For private parties there’s the Kingpin Suite with four lanes and seating for up to 70 people. Also here is a laser tag arena, an arcade, axe throwing, an arcade with new games and classics, a VR attraction, and finally social games like billiards, giant jenga, cornhole and ping pong.

9. Casey Pool

Swimming PoolSource: Roman Samborskyi / shutterstock
Swimming Pool

Near the line with Hopedale, by the Milford Regional Medical Center, there’s a public outdoor pool run by the Massachusetts Department of Conservation & Recreation.

This is a small-ish facility but has more than enough to keep youngsters entertained in the school summer break, and offers swimming lesson programs throughout the season.

There’s a training pool for lap swimming, adjoining a wading area with zero-depth entry. The season kicks off in late June, and the basic facilities include restrooms, showers and lockers.

10. Plains Park

SwanSource: Yingna Cai / shutterstock

This well-kept park has a pretty setting, on the eastern shore of Milford Pond, within a mile or so of the town center.

Around the Fourth of July, Plains Park is the place to come to see Milford’s annual fireworks show, and also hosts a number of other Lions Club events throughout the year, including a car and truck show in September that has been held since the 1980s.

In the warmer months Plains Park is somewhere to come and admire the waterfowl, and take a picnic at the large shelter. A winding trail takes you close to the water, and past a trio of fields used by Milford Youth Baseball.

11. Basic Batch Donuts

DonutsSource: Tibor Duris / shutterstock

Another of the exciting independent businesses to check out in Milford is this specialty donut shop, just off the Upper Charles Trail at 206 E Main St.

Basic Batch Donuts prepares its dough before sunrise to ensure every batch is as fresh as possible, has scratch-made pastries and serves coffee supplied by Red Barn Coffee Roasters in Upton, MA.

Donut-wise there’s a mix of cake and yeast-style, with classic options like honey glazed and outlandish creations such as maple bacon and fruity pebbles.

12. Little Red Shop Museum

Little Red Shop MuseumSource: Yingna Cai / shutterstock
Little Red Shop Museum

To the southwest, the town of Hopedale is contiguous with Milford and for decades up to the 1980s was the home of the Draper Corporation, the country’s largest manufacturer of power looms for the textile industry.

Hopedale’s industrial heritage, and the history of the wider Blackstone Valley, is detailed at this pondside museum, housed in the oldest industrial building in the town.

The Little Red Shop (c.1845) is the humble old machine shop in which Ebenezer D. Draper made loom temples in the mid-1800s. By the end of the century the Drapers would dominate the loom-making business.

Exhibits go into depth on those early days, the history of the Draper Corporation, and Hopedale’s Draper-funded development after incorporation in 1886.

13. Mendon Twin Drive-In

Mendon Twin Drive-InSource: John Phelan / Wikimedia | CC BY-SA 4.0
Mendon Twin Drive-In

When we put this list together there were just three drive-in theaters still operating in Massachusetts, and one of these is less than ten minutes from Milford Center.

The Mendon Twin Drive-In is held in such high esteem, and has moved so smartly with the times, that it’s hard to see it ever disappearing. With space for 800 cars, the theater opened in 1954 and added a second screen in 1998.

Audio is via FM radio instead of speakers on poles, and both screens have up-to-date digital projection and Dolby Digital sound.

The popcorn is made fresh on the premises, and there’s a full menu of comfort food, from pizza to soft serve. Another recent change is Pop’s Beer Garden, a 5,000-square-foot patio with a view of Screen One, serving craft beer and wine by the glass.

14. The Pumpkin Farm

PumpkinsSource: xsense / shutterstock

Just out of Medford on Route 109 (Milford St) there’s a diversified farm known for its pumpkins, but also growing a range of other produce, and raising beef, lamb, pork, chevon and chicken.

This is sold at a small stand at 72 Milford St, which is unstaffed and uses the honor system, recently updating its freezer system and now making it possible to check out with a credit card.

The farm employs sustainable practices, using no synthetic fertilizer, pesticide, fungicide or herbicide, while the livestock has a lot of outdoor access in open fields or woods.

15. Echo Lake

Echo LakeSource: Nishan Nishman Bilazarian / Facebook
Echo Lake

This reservoir next to the Nemba property is just over the line in Hopkinton and serves as Milford’s water supply. Echo Lake is also significant as the source of the Charles River.

Because of its role as an active reservoir, no recreation is allowed on the lake. But you can get close to the shore to appreciate the sublime views on a recently built trail.

This starts along Granite Street on the north side, and follows the former CSX right-of-way. During the short walk you’ll come across interpretive boards documenting the granite quarrying that used to take place here.


15 Best Things to Do in Milford (MA):

  • Upper Charles Trail
  • Memorial Hall
  • NEMBA Trails at Milford (Vietnam)
  • Main Street Milford
  • CraftRoots Brewing
  • Depot St Tavern
  • Peppercorn Hill Conservation Area
  • PiNZ Bowl Milford
  • Casey Pool
  • Plains Park
  • Basic Batch Donuts
  • Little Red Shop Museum
  • Mendon Twin Drive-In
  • The Pumpkin Farm
  • Echo Lake