On just seven square miles, this town east of Brockton is one of the smallest by area in Massachusetts.
Known for its shoemaking trade in the 19th and early 20th century, Whitman got its name from a local philanthropist in the 1880s, shortly after being made a township.
Dairy farming has also been a way of life in Whitman for centuries. One farm, Peaceful Meadows, went into the ice cream business in the 1960s and has a stand that has been going strong for more than 60 years now.
On the subject of sweet treats, Whitman is the birthplace of the Toll House cookie, invented at the Toll House Inn in the 1930s by Ruth Wakefield, who figured out a mutually beneficial deal with Nestlé that led to the recipe being published on their packaging.
1. Whitman Center
At the intersection of Washington Street and South Avenue, and continuing north, south and east for a few blocks, Whitman has a great little downtown area.
There’s an august Town Hall building, constructed in the Colonial Revival style at the turn of the 20th century. Behind it sits Whitman Park, where many of the town’s outdoor events take place in summer.
On the streets are a small but strong roster of coffee shops, pubs and restaurants, some of which have been a fixture for decades, like Millie’s Lunch (founded 1971), and The Venus Cafe (1964).
2. Whitman Town Park
The prominent local citizen, Augustus Whitman (1821-1880), for whom the town is named, gifted this 14-acre parcel of land for a public park in 1880.
The famous Olmsted Brothers landscape architecture firm provided the design, which was completed by the early 1900s.
Many elements from their plans are still here, among them a bandstand, wading pool, grand drinking fountain and a tennis court that is now used for basketball.
The firm was called back in the 1930s to make improvements to the drainage and update the design to fit the Civil War Monument, erected here in 1908.
The paths here wind past lofty oaks and pines, the amenities include a large picnic area, a pond with lots of waterfowl, and the best children’s playground in the town.
3. Peaceful Meadows Ice Cream
On the map for decades, this ice cream-focussed farm stand in Whitman is open all year round. The dairy farm at Peaceful Meadows goes back all the way to 1920, and has been serving its homemade ice cream here since the stand opened in 1962.
Every part of the process, from the development of new flavors to miking and freezing takes place at this site. As well as some 25 flavors, there’s a choice of sundaes (including create your own), shakes, ice cream cakes and frappes.
As well as the ice cream, almost everything is homemade, from the waffle cones to the syrups, cookies and brownies. The store here also sells fresh milk, bake-at-home pies, and seasonal dairy items like eggnog.
4. Hobart Pond
Something great about Whitman Center is that Whitman Park is just one element of a large swath of public green space. This includes the sports facilities at Memorial Field to the north, but also the picture perfect conservation land at Hobart Pond.
Here you’ve got a fantastic place for a walk without having to get in your car and leave the downtown area. An unbroken paved trail, dubbed The Boulevard, runs along the south shore of the pond.
Between Essex Street and South Avenue, this passes venerable evergreen trees and a line of benches for a third of a mile.
Hobart Pond is manmade, and has been here since the 17th century, with a water-powered mill at the South Avenue.
This started as a sawmill, becoming a gristmill by the 1730s, and then an iron foundry and munitions factory by the late 18th century.
5. Old Colony Brewing
Worth keeping on your radar in Whitman Center is a pocket-sized craft brewery with an assortment of quality, handcrafted beers on tap.
Normally open weekends, Old Colony Brewing (OCB) was founded by four Whitman natives in 2013 and recently moved into a commercial space downtown.
There’s a condensed list of brews on tap here, led by Moneyline (IPA), Whitman Wheat, OCB Hard Seltzer (several flavors), Hoppy Patriot (IPA), and a variety of seasonal beers like Poolside American Wheat Beer, Snow Day Spiced Porter and Pumpkin Ale.
There’s always something happening here, from seasonal celebrations to a run club, music bingo and sports nights.
6. Whitman Day
When we made this list, Whitman had recently launched a summer celebration taking place on a Saturday in June at Whitman Park.
Supporting the Whitman Food Pantry, Whitman Day has a schedule filled with fun and free activities for all ages. First off, there’s a program of live music with five or more acts, along with extra performances at the bandstand.
You’ve also got a puppy parade, an art tent, a diversity of food options, as well as demonstrations for everything from dance to yoga to robotics.
For kids, the best part may be the Touch a Truck event, where they can get behind the wheel of local service vehicles, including fire and police, as well as a tactical rescue truck.
7. Ames Nowell State Park
A couple of miles from Whitman, this 700-acre state park is steeped in history reaching back to the 17th century.
Among the many clues of human habitation are an extensive network of stone walls, a pair of quarries from the 1600s and 1700s, and two wagon bridges.
The man who made the biggest impact on the landscape at Ames Nowell State Park was the wealthy lawyer Edwin Holmes, who dammed Beaver Brook in the 1920s to form Cleveland Pond, in an effort to create a bird sanctuary here.
Nowadays this is a place for fishing and hiking, with several miles of trails along the edge of the pond and into the woods, complemented by a picnic area.
8. The Venus Cafe
Bar pizza has been a culinary forte of the South Shore for decades, but had really come into fashion around the time we wrote this article.
With a thin, cracker-like crust, these personal pies are usually baked in round 10″ pans until the cheese has an enticing crust. Easily missed in an unprepossessing building at 47 South Ave, The Venus Cafe has been in downtown since 1964.
As well as conventional toppings like pepperoni, sausage, onion, mushroom and bacon, you can also get sweet pizzas here, with the likes of blueberry, apple cinnamon and oreo.
9. Donald Flaherty Trail
Along Auburn Street, near the intersection with Washington Street you can embark on a little walk in nature on this unfrequented trail.
Just under a mile out and back, the Donald Flaherty Trail is announced by a large wooden sign reclaimed by the undergrowth and easy to miss.
On an old cart path, the trail runs along an embankment next to wetlands that are drained by Meadow Brook. If you go quietly you stand a good chance of seeing a lot of birdlife in the marshy areas, with great blue herons often sighted here.
There are several short spurs leading off the main path, one taking you west to St. James Cemetery.
10. Strawberry Valley Golf Course
Within shouting distance of Whitman in Abington is a well-regarded, 9-hole public course, owned by the Town of Abington and dating back to 1965.
If you’re on the hunt for a forgiving track, primed for new players, or just want to refine your iron game, this municipal course checks most boxes.
The level of maintenance is consistently praised, and the greens are true. As this is a public space, the undulating landscape becomes a winter wonderland after snowfall, perfect for sledding and cross-country skiing.
11. Carousel Family Fun Center
On the scene in Whitman for two decades now, the main attraction at Carousel Family Fun Center is an indoor roller skating rink.
In the best way, this is like a nostalgic throwback to rinks of the 1980s, with a giant, sleek wooden surface, disco lights, and star motifs on the walls.
The center caters to all ages, providing lessons for basic, intermediate and advanced levels. Wednesday is family night, and there’s a host of seasonally themed events all year round.
Also check the calendar for adult nights, soundtracked by a mix of soul, disco music, R&B, house and reggae.
12. Toll House Inn Site
In Whitman, a parking lot between a Wendy’s and a Walgreens is the place to come for an unexpected piece of modern history.
Here a sign and accompanying plaque mark the site of the Toll House Inn, which stood here from 1817 until it burned down in 1984.
The inn was made famous by proprietor Ruth Wakefield (1903-1977), who developed a recipe for chocolate chip cookies in the 1930s, using butter drop dough and Nestlé’s semi-sweet chocolate.
The cookies were a hit, and Wakefield struck a deal with Andrew Nestlé, allowing the company to print her cookie recipe on their Semi-Sweet Chocolate Morsels packaging, in return for a lifetime supply of chocolate.
13. 10th District Brewing Company
Beer aficionados will be pleased to know that there are two craft breweries awaiting you in the Whitman Area.
Founded in 2014 by two childhood friends, 10th District Brewing Company is just five minutes away in Abington and is poured at a growing number of restaurants and bars in the area.
The taproom here has a stripped-back interior, with a sunny patio, and a big window behind the taps into the brewery itself.
There are more than a dozen beers on draft at any time, with simple, style-based names like Extra Special Bitter, India Pale Ale, American Pale Ale, Vanilla Porter, Tripel and Double IPA.
14. East Bridgewater Cinemas
South Shore Cinemas runs two movie theaters close by, at South Weymouth, and just a couple of miles out of Whitman at East Bridgewater.
Originally opened in 1991 and passed between several owners, this five-screen multiplex is at the Carriage Crossing Shopping Center, and is a refreshing change from the big theater chains.
The difference is most noticeable in the personalized service from the employees, and in the pricing for tickets and concessions, which is half as much as you would expect to pay at other spots.
You still get all the latest Hollywood releases, with excellent picture and sound quality, and comfortable seating.
15. Summer Concert Series
Maybe the best way to spend a balmy summer evening in Whitman is at a free concert, funded by the Massachusetts Cultural Council.
These are held on Thursdays June through mid-July at the gazebo at Whitman Park, and you’re free to bring a lawn chair or picnic blanket.
Concerts begin at 6:00pm, and there’s a new style with each performance, running the gamut from oldies to country, soul, rock, funk, folk and even shows by the Defenders Drum and Bugle Corps.
In late June there’s an additional show on Saturday to coincide with the Whitman Day celebrations.