Sitting about 25 miles northwest of downtown Boston, Littleton is a town with a Colonial history reaching back to 1645. It was here that the Puritan missionary John Eliot established the sixth Praying Village, inhabited by Native American converts.
Known as Nashoba, the village was located between Fort Pond and Lake Nagog, much of which is now taken up by the Sarah Doublet Forest, named for the last “praying Indian” who died in 1736. Today Littleton is the New England headquarters for the technology giant, IBM, and benefits from massive tracts of conservation land containing overlooks, a ravine, caves, and mature lakefront forest.
1. Long Pond
A lovely natural feature within shouting distance of Littleton Common is this 113-acre Great Pond.
Despite being so close to the center of town, Long Pond is surprisingly free of development, with the southern and western portions of the shoreline ensconced in conservation land.
Open Memorial Day weekend through Labor Day, Littleton’s public beach sits on the northwest shore, and is a fine place to unwind or cool off on a hot day.
There’s a good sweep of sand, a bathhouse, a kayak/canoe launch and picnic areas. You can purchase seasonal membership or pay a daily use fee.
2. Kimball Farm
Next door in Westford, this cherished family entertainment center attracts people from all over New England.
Dating back to 1939, Kimball Farm is a dairy farm that has added a host of attractions over time. If golf is your game, you’ve got two 18-hole adventure golf courses, a 9-hole pitch & putt course, and a driving range with 75 hitting stations.
Beyond that there’s a zipline, batting cages, bird of prey demonstrations, pony rides, a petting farm, bumper cars, bumper boats, and an arcade.
Kimball Farm is equally famous for its creamy homemade ice cream, which comes in more than 50 flavors.
There are two places on the farm where you can order hot food, one of which is a classic New England seafood shack making regional fare like lobster rolls, clam strips, fried scallops, and hand-cut onion rings.
3. Nashoba Valley Tubing Park
The Nashoba Valley Ski Area is on the Littleton-Westford line, and for many people the main attraction is the giant snow tubing park on a deceptively steep hill.
With as many as 18 lanes, served by four lifts, this is officially the largest tubing park in New England.
You’ll pay for a two-hour slot, and will then be free to make as many runs as you want. The lanes are carefully maintained, and are suitable for everyone over 42” in height or 6 years old.
Doubles and group tubing are permitted, depending on the conditions. As you can imagine, the experience depends on the weather—if you visit after fresh snowfall the lanes will be a little slower.
4. Nashoba Valley Ski Area
The entrance for the tubing park is in Littleton, while the main ski area is accessed from the Westford side of the town line.
This small mountain has been open to the public since 1964, and is known for having one of the best terrain parks in the state. With a vertical difference of about 240 feet, the Nashoba Valley Ski Area has 17 runs, the longest of which is 1,400 feet.
The area has four conveyor lifts, four chairlifts and three rope tows, which keep things flowing with a capacity of 11,600 per hour.
The on-site Outlook Restaurant is open all year round, and outside the winter season there’s a summer camp for kids, and Witch’s Woods, one of the top Halloween scare experiences in the region.
5. Prouty Woods
One of the best places for a walk in Littleton is the town-owned stand of mature woods on the western shore of Long Pond.
Prouty Woods has some 1,600 feet of lake frontage, and the picturesque woods on the shore have a vital ecological purpose, ensuring the purity of the lake’s watershed and preventing erosion.
Another essential natural feature at Prouty Woods is Wilderness Hill, which climbs to 170 feet over the surrounding land.
Thanks to its prominence the views from the summit are astonishing on a clear day, with Mount Monadnock visible around 35 miles to the northwest and Mount Wachusett on the western horizon, about 20 miles away.
Come in early spring and you can witness the bizarre courting ritual of the American woodcock, known as the “Sky Dance”, in which the male soars 350 feet in the air before descending in curious zigzag style, while generating strange noises with their special wing feathers.
6. O’Neil Cinemas
This sleek multiplex opened at Littleton’s The Point shopping center in 2017. With eight screens, the theater is part of a small chain in New England, delivering a state-of-the-art movie experience in a sophisticated ambience.
There are recliners throughout, complete with drink holders and trays, and you’ll be wowed by the latest sound and picture technology in every screen.
But the star is the Grand DLX, billed as the largest screen in Boston’s Metro Northwest, at 72 feet across and four stories high, with multidimensional Dolby Atmos sound.
In keeping with the upscale feel, there’s the Backstage Lounge, a full-service eatery/bar, with a 15-foot video wall showing sports events, trivia and more.
7. Oak Hill Conservation Land
You could easily spend hours exploring the trails at this large conservation property in the west of Littleton and not get bored.
There are seven miles of trails at Oak Hill, with plenty to be discovered as you go. One highlight is Lookout Rock, rising to 475 feet above sea level, and with views that take in Boston’s Prudential Tower and John Hancock Tower (26.5 miles to the southeast) on a clear day.
Also thrilling is Tophet Chasm, dropping 80 feet at the site of what was once a monumental waterfall at the end of the last Ice Age.
Incorporated into the trail system at Oak Hill are a pair of 19th-century stagecoach roads, and if you look closely you can see where the wheels of these coaches cut grooves into the bedrock.
8. Smith Conservation Land
South of Oak Hill and overlapping into Harvard you’ll find this treasured conservation area, mixing wetlands, open fields and former farmland on just over 60 acres.
The Smith Conservation Land straddles Whitcomb Avenue, offering very different experiences on each side.
To the west, you’ll travel along an unforgettable ravine perforated with caves that are known to provide a shelter for porcupines, coyotes, bobcats and even black bears.
Things are gentler east of Whitcomb Avenue where the trail skirts the edge of the marshes on Beaver Brook, with distant views of a great blue heron rookery if you have binoculars with you.
9. Spring Brook Farm
Covering more than 400 acres, this farm in the north of Littleton can trace its history back all the way to 1713.
Even more remarkable, Spring Brook Farm has been in the same family since that time. Ten generations later, the farm remains a vital community asset, valued for the home-grown and homemade products on the shelves of its country store.
Think freshly picked fruits and vegetables, eggs, honey, plants, the farm’s popular line of jams, farm-raised meats, and a bounty of baked goods, from fresh breads to pies, quiches and cookies.
The store also has a trove of charming gifts like candles, jewelry, linens, and decorations for interiors and gardens.
10. Sarah Doublet Forest
The Littleton Conservation Trust’s largest property is 100 acres of woods on a piece of the historic Nashoba Plantation.
There’s an exciting mix of natural abundance and history to be discovered along a warren of blazed trails at the Sarah Doublet Forest.
The yellow loop traverses former pasture and passes a long abandoned quarry, while the red loop passes vernal pools and a patch of witch hazel shrubs, which are stunning in fall when their yellow flowers are in bloom.
Close to the parking lot on the orange trail you’ll see the mysterious remnants of an old farmhouse, with only a chimney stack and foundations remaining.
11. Houghton Memorial Building
One of the finest pieces of architecture in Littleton is the former public library building, now home to the Littleton Historical Society.
Built with yellow brick and completed in 1895, the Houghton Memorial Building is in a Colonial Revival style, with Romanesque Revival elements on the main facade.
This was a gift from the son of William S. Houghton, a wealthy Boston merchant who was a Littleton native and had earlier funded the library’s collection.
When we wrote this article the building was open on Wednesday afternoons and occasional Sundays. Head inside for enlightening exhibits about various aspects of local history, as well as for seasonal gifts at the museum shop.
12. Bobby’s Ranch
Close by in Westford there’s an equestrian business that dates right back to 1972. Bobby’s Ranch started out as a way to keep the namesake proprietor, Bobby, occupied during the summer as a 16 year old.
The ranch flourished over time and is now run by Bobby, his wife Celia and their daughters Cassie and Theresa.
There’s a boarding service, a horsemanship program for kids in summer, and a menu of private, semi-private and group horse riding lessons.
But the ranch’s main business is a guided trail riding service (by reservation). On docile and friendly horses, these take place in bucolic rural scenery, and you can even go on a weekend-long adventure if you book in advance.
13. The Point
When it opened to the public in 2015, this mixed-use development became the first of its kind in Boston’s Metro Northwest region.
The Point is just off I-495 and integrates a hotel (Courtyard by Marriott), offices, entertainment attractions, and a selection of stores, eateries and other service businesses.
Hand-in-hand with O’Neil Cinemas, one of the best things going for The Point is its food scene.
At close quarters you can choose from Indian, pan-Asian, tavern fare, and New England-style seafood.
There’s also a wine bar, and locations for Starbucks, Anthony’s Coal Fired Pizza & Wings, and Moe’s Southwest Grill.
14. MetroRock Littleton
Opened in 2019, this indoor climbing gym at The Point is part of a regional chain, catering to climbers of all abilities.
After signing a waiver and picking up any necessary gear, experienced climbers can start exploring the bouldering terrain at MetroRock within minutes of arriving.
There’s a test for top-rope climbing, and a more stringent assessment if you’re here for lead climbing.
Novices are free to drop in anytime, and will be given a thorough orientation, and a tutorial on how to use the auto-belays.
If you’d feel more comfortable with a guided intro to climbing you can book a private belay, and will be talked through the techniques by a member of staff.
15. Shaker Hills Country Club
Moments away in Harvard there’s a publicly accessible golf course with a high reputation. In its time, Shaker Hills Country Club has been listed as the top public course in Massachusetts, and this prestige is reflected in the green fees, which are at the upper end of the market.
The current layout goes back to a renovation in 2012, and one of the course’s biggest assets has always been its spectacular, rambling scenery.
As a fitting finale, you’ve got a breathtaking 560-yard dogleg par 5, ending at the clubhouse. This facility is perched above a natural amphitheater, with views of the 1st, 9th, 10th and 18th holes from the top deck.