This suburban city is on the South Shore, at the foot of the Blue Hills, which pass by to the north.
Randolph is great if you love the outdoors, with many of the most cherished spaces in the Blue Hills Reservation state park close by, like Ponkapoag Pond, renowned for its Atlantic white cedar bog.
In the summer you can swim in lakes around Randolph, and experience some of the Blue Hills on horseback via one of the equestrian centers on the edge of the state park.
The South Shore has a reputation for its bar pizza, a style of personal pizza made famous by spots like Lynwood Café, opened in Randolph in 1949 and still going strong.
1. Blue Hills Reservation
Randolph is on the edge of a 7,000 acre state park containing the Blue Hills, which comprise the highest point in the Boston area. This is Great Blue Hill (635 ft), named by early colonists for the blueish tone of its granite.
The Blue Hills Reservation puts an almost endless choice of recreation opportunities at your fingertips, from skiing in winter to swimming at lakefront beaches in summer.
For awe-inspiring views you can make the short drive to a trailhead for the rocky Skyline Trail, crossing the ridge for 7.5 miles, with downtown Boston and the harbor on the horizon to the north and northeast.
A good starting point for any visit is the reservation’s headquarters in MIlton, where you can purchase trail maps for hiking and mountain biking.
2. Ponkapoag Pond
In the very south of the Blue Hills Reservation there’s 203-acre impoundment, with shores that are completely free of development, save for a dock, canoe launch and the AMC Ponkapoag Camp.
The entire pond is ringed by a walk trail, more than four miles long and served by three different parking areas.
There’s also a boardwalk, more than 1,000 feet in length, crossing the pond’s expansive white cedar bog, and undergoing repairs when we wrote this list.
Pickerel, bass and panfish are commonly caught at Ponkapoag Pond, while the AMC Ponkapoag Camp offers 20 cabins and two tent sites for year-round rental.
3. Lynwood Café
Personal bar-style pizza, made with 10” pans are a South Shore specialty, originating in establishments like the Lynwood Café, with cheese and crust going to the very edge of the pan.
This neighborhood bar opened in 1949 and uses a family recipe and quality local ingredients to make what many argue is the essential bar pizza.
There’s a choice of a dozen toppings, available to order in an endless array of combinations. Linguiça spicy sausage is a variation typical of the South Shore, but one topping specific to the Lynwood Café is Boston Baked Beans.
4. The Bradley Estate
The Trustees of Reservations manages this 90-acre estate, with woods, meadows, pastures and formal gardens around a stately Colonial Revival house.
Much of the estate, including the house, was designed in 1902 by Charles A. Platt (1861-1933), part of the American Renaissance movement.
The property was bequeathed to the Trustees of Reservations in 1991, and is open to the public, for easy strolls around a beautiful walled garden, parterre and three miles of wooded trails that take you past the estate’s farm.
The house is rented out for private events, and is the centerpiece for a stunning light show in the holiday season.
5. Randolph Center
At the busy intersection of Route 28 (Main Street) and Route (139), Randolph has a low-key downtown area with a smattering of local businesses and a few interesting sights.
The most prominent of these has to be the grand Stetson Hall (1842), Randolph’s Greek Revival former town hall, dating to 1842 and now used as an events venue.
There’s a roster of dining options, from pho to pizza, and a few local shops for jewelry, collectibles and electronics, and the treasured Turner Free Library that was established in 1874.
6. Houghton’s Pond Recreation Area
On a warm summer’s day one of the best places to be is on the shores of Houghton’s Pond in the Blue Hills Reservation. At 24 acres, this is a kettle hole pond formed by retreating glaciers at the end of the last Ice Age and fed by a spring.
On the north shore is a sandy beach, about 800 feet long and with lifeguards on duty every day from mid-June to Labor Day.
The recreation area was improved during the Great Depression by the Civilian Conservation Corps (CCC), and there’s a visitor’s center with memorabilia from that time, and a refreshment stand listed on the National Register of Historic Places.
The pond is stocked with trout for fishing, and there are trails, grills, picnic tables, a ballfield and a playground for kids.
7. Powers Farm
The Town of Randolph acquired this ecologically important parcel of land in 2009. On 22 acres Powers Farm had been worked by the same family since the 19th century, and long-term agriculture had kept the landscape free of invasive plant species.
Now you can come to wander in this mosaic of habitats, including brooks, successional meadows, a rare Atlantic white cedar swamp, marshland and an alfalfa field.
The property comprises the picture-perfect Norroway Pond, built over a century ago for ice production and water supply, and today a haven for waterfowl and other fauna.
8. Daddy’s Dairy
This mini-chain of ice cream parlors has five locations, all within a few minutes of each other on the South Shore.
Opposite Powers Farm, the Randolph branch offers more than 80 flavors of ice cream flavors, with plenty of out-there options like Cake Batter, Cotton Candy and Funfetti Cake.
There are also 200+ soft serve flavors, from Almond Joy to White Chocolate Mousse, along with a massive choice of toppings, whether you want fresh fruit, nuts, broken cones or popping boba.
You can even treat your dog to an ice cream here, and there’s a lineup of freshly made ice cream cakes and pies in the freezers.
9. Central Rock Gym
Also on the edge of the Blue Hill Reservation is an indoor climbing center with 18,000 square feet of climbing terrain, a 45-foot lead wall, 3,000 square feet of bouldering and 100 top rope and lead stations.
Newcomers and kids can get to grips with the basics on an hour-long staff belay session, scheduled in advance.
Solo climbers can make use of auto belays, which require a brief orientation session, and if you’re here with a partner there’s top-roping, preceded by an hour-long class teaching you the knots and belaying techniques.
After that you can use the gym with a day pass and sign up for a variety of more advanced classes.
10. Jonathan Belcher House
A little way north of downtown Randolph, this grand Federal-style house was built in 1806 by one Jonathan Belcher (1767-1869) and his wife Abigail.
Their descendants added to the house, before their great-granddaughter, Abigail Tower Tarbell gifted the property in 1911 to what is now the Randolph Women’s Club.
The house occasionally hosts yard sales, as well as an annual holiday fair. Opposite, you can follow the alley-like Park St to Belcher Park, which has a beautiful little pond and a handful of facilities like a climbing wall, ropes course, basketball courts and a soccer field.
11. Blazing Saddles Equestrian Center
One of the best ways to encounter the Blue Hills Reservation is on a horse, and if you don’t have your own, there’s an equestrian center/stables by the reservation in Randolph.
Blazing Saddles has a large farmyard and indoor equestrian arena, and you can bring younger children for a ten-minute ride, hand-guided by a member of staff.
Trail rides in the Blue Hills Reservation (eight years and up) range from 30 minutes to an hour, and are open to novice riders.
12. Blue Hills Ski Area
On the west face of Great Blue Hill is a ski area that opened in 1950, and has now helped several generations find their feet on the snow.
The Blue Hill Ski Area is on 60 acres, with eight runs, four lifts and a vertical drop of just over 300 feet. Snow-making capacity has been increased year-on-year, for a winter-long skiing season.
There are ski programs for all ability levels and ages, or you can book one-on-one lessons for more focused tuition. Finally, in terms of equipment there’s a choice of daily rental packages.
13. Imagination Station
The largest community playground in Randolph has been designed with a lot of love. The Imagination Station has areas themed on an enchanted forest, prehistoric jungle with dinosaurs and a savanna roamed by lions and cheetahs.
The playground is fully accessible, and has ample, well-positioned seating so children will always be in view. You’ll also find a sound playground for budding musicians, a splash pad open during the summer months and a shaded pavilion for picnics.
14. Ponkapoag Golf Course
This 36-hole municipal golf facility, designed by noted course architect Donald Ross, is on the western shore of Ponkapoag Pond.
A consistent feature of Course #1 and #2 is the rolling terrain, with some challenging jumps in elevation.
The blissful wooded scenery is one of the facility’s great selling points, and in the winter the entire landscape becomes a park for cross-country skiing. Complimentary amenities include a pro shop, snack bar, putting green and a driving range.
15. Showcase Cinema De Lux Randolph
Descending two levels underground is this massive, 16-screen, four-storey multiplex that opened in 1998.
Showcase Cinema De Lux Randolph has raked seating and luxury recliners in all of its theaters, as well as high-end Dolby Surround Sound and large screens. There are IMAX and 3D screens here, as well as a 4D theater with moving seats and ambient effects.
One benefit of the Lux level, added in the 2000s, is food and alcohol service, while Bargain Tuesdays bring discounts all day, with extra savings for “Starpass” members.