Bordering Connecticut and also close to the Rhode Island state line, Webster is a town in Central Massachusetts famed for its magnificent lake.
Long before European colonization, Lake Chaubunagungamaug was part of the ancestral home of the Nipmuc people for millennia.
The town’s modern era began in the early 19th century when the important industrialist Samuel Slater constructed textile mills, powered by the lake. He named the new settlement after his friend, the statesman Daniel Webster (1782-1852).
Later, the lake’s undeniable beauty established Webster as a resort town. In the early 1920s this was given the novelty 45-letter name, Lake Chargoggagoggmanchauggagoggchaubunagungamaugg, which is the longest name of any natural feature in the country, and one of the longest in the world.
1. Webster Lake (Lake Chargoggagoggmanchauggagoggchaubunagungamaugg)
Webster goes hand-in-hand with the 1,442-acre great pond that sits east of I-395. Lake Chargoggagoggmanchauggagoggchaubunagungamaugg was an important fishing location for the Native Americans, powered the town’s textile mills and later brought vacationers to the town.
Despite its industrial past, this is a natural body of water, formed by retreating glaciers at the end of the last Ice Age, and fed by streams and underwater springs.
While Webster Lake isn’t vast, the shoreline is a jumble of peninsulas and coves, adding up to 17 miles of waterfront, with eight islands.
We’ll talk later about some of the attractions around the shore, but if you want to get onto the water you can head for Lakeview Marina (311 Thompson Rd), which is a full-service marina renting out kayaks and stand-up paddleboards mid-May through Columbus Day.
2. Memorial Beach
The town’s public beach at Webster Lake is on a peninsula on the lake’s northwestern shore. Memorial Beach is a spotless sweep of coarse sand, next to a shallow swimming area, a couple of hundred feet in length.
The view from the beach is sensational, and you’ll find all you need for a family day out, with a playground, changing facilities, picnic tables, a basketball court and a large wooded area behind and at the tip of the peninsula.
For non-residents arriving by car, it makes sense to be here on weekdays when the parking charges are much lower. If you can get here by bike or on foot the entrance fee is negligible.
3. Indian Ranch
Dubbed “New England’s Home of Country Music”, Indian Ranch is a seasonal live music venue and resort on the northern shore of Webster Lake.
The roots of Indian Ranch go back to 1943, and the list of country music luminaries that have performed at this 3,046-capacity amphitheater is a who’s who of the genre.
Think Johnny Cash, Willie Nelson, and Tammy Wynette, while Kip Moore, The Marshall Tucker Band, Melissa Etheridge, Jamey Johnson and “Weird Al” Yankovic are just a few of the recent performers.
The 180-site campground here is open May through mid-October, and there’s an on-site restaurant, conference space, and the Indian Princess paddlewheel boat for cruises.
4. Indian Princess
At Indian Ranch you can step aboard an accurate modern replica of the elegant riverboats that navigated the Mississippi in the 19th century.
The Indian Princess is one of the few authentic vessels of its kind, powered exclusively by split stern wheels that are driven by twin diesel engines.
With many riverboat replicas the wheels are just ornament rather than a means of propulsion, but the Indian Princess is the real thing.
There’s a schedule of public cruises on Lake Webster in the summer months, and this unique vessel can be rented for anything from corporate parties to weddings. Inside, the Princess Dining Room has a full bar, galley and a large flatscreen TV.
5. Samuel Slater Experience
You could say that Webster owes its creation to the English-American industrialist Samuel Slater (1768-1835). He is remembered as the “Father of the American Industrial Revolution”, bringing British textile technology to the young United States.
Attracted by the inexhaustible water power of Webster Lake, he relocated to the area in the 1810s, established several mills and named the town after his friend, Daniel Webster.
Opened in 2021 at a repurposed building by Memorial Athletic Field, the Samuel Slater Experience is an interactive museum going into detail on Slater’s personal story, and recalling Webster’s textile manufacturing origins.
There are more than 20 immersive and artifact-filled exhibits, detailing his crossing, his innovations, the life of a worker, early Webster, and the town’s emergence as a 19th-century resort.
6. Downtown Webster (Main Street Historic District)
On Main Street, from the railroad tracks east to the Webster’s Town Hall, you’ll enter a well-preserved central commercial district from the end of the 19th century.
Up to four storeys tall, the impressive brick commercial blocks bear the dates of their construction and the names of the people who built them.
Among the most imposing is the Racicot Block (1905), now used by MAPFRE Insurance, which is headquartered in Webster.
Here and further along Main Street you’ll find several places to eat, whether you’re in the mood for pizza (Northeast Pizza), pan-Asian (Eastern Pearl), traditional Italian (Monte Bianco), modern American cuisine (Stave & Still), and there’s a handful of bars.
On the north side, French River Park is crossed by a section of the French River Greenway, which will eventually run for seven miles through the area.
7. Douglas State Forest
Running the length of Webster’s eastern flank is almost 6,000 acres of protected nature, sweeping down to the borders with Rhode Island and Connecticut.
Whether you’re up for some hiking, mountain biking, horseback riding or cross-country skiing in winter, Douglas State Forest is a dream.
The forest is crossed by two long-distance trails, in the 22-mile South New England Trunkline Trail, and the 92-mile Midstate Trail, which both run close to the tri-state point (more below).
Within the park’s boundaries is a large piece of the Wallum Lake shore, for activities like swimming, boating and picnicking in summer. Also important is a rare parcel of Atlantic white cedar swamp, ready to be experienced on a special boardwalk trail.
8. Tri-State Marker
At the exact southwestern corner of Douglas State Forest is the state’s border with Connecticut and Rhode Island.
Although the location is significant, the tri-state marker is pretty remote, buried deep in hardwood forest, but relatively easy to reach on foot.
To get there you could walk the Midstate Trail or the Southern New England Trunkline Trail, both of which pass close by and have connecting spurs.
On a ridge there’s a little granite monument, erected in 1883 and pointing out the orientation of the three states.
9. Pierpont Meadow Wildlife Sanctuary
The Massachusetts Audubon Society manages this 211-acre landscape where nature has reclaimed a parcel of old farmland.
Historic stone walls still delineate the meadows at Pierpont Meadow Wildlife Sanctuary, and weave through pine forest that has since taken over.
This preserve is also known for its ecologically important shrubland, serving as a crucial nesting habitat for the eastern towhee and brown thrasher, which are in decline in the region.
A great time to visit is at the height of summer when the meadows are illuminated by fireflies, while beavers can be observed later in the day by a small pond near the entrance.
10. Breezy Picnic Grounds & Waterslides
Next to the Whitin Reservoir, just east of Douglas State Forest there’s a family recreation attraction that has been a summer staple since 1953.
On the lake there’s a large swimming area with sandy areas that kids are sure to love. These are backed by a lovely grassy area with large picnic tables and a lot of shade beneath the trees.
You’ve also got a snack bar on hand for comfort food and cold treats like soft serve. Maybe best of all for kids and teenagers, there’s three 300-foot waterslides, and a smaller slide for little ones, 42” and under.
11. Mohegan Bowl
Now fitted with a new, sleek interior and the latest scoring technology, this bowling alley dates all the way back to 1958 and has been under its current ownership since 2012.
At Mohegan Bowl you can choose between a game of ten-pin bowling and the regional variation, candlepin bowling, which originated not far away in Worcester in the late 19th century.
In the same complex you’ve also got a laser tag arena, as well an arcade with a redemption center.
Although this alley has been totally modernized, classic comforts like cold beer and fresh baked pizza are still central to the experience.
12. Thompson Speedway Motorsports Park
There was a time when this fabled racetrack, ten minutes south of Webster in Thompson, CT, was known as the “Indianapolis of the East”.
Thompson was the first asphalt paved oval track in the country when it opened in 1940, and the heyday came in the late 1960s and early 1970s, when there were NASCAR Cup Series races here.
This is still an exciting venue for motorsports, especially in fall when the NASCAR Whelen Modified Tour comes to town, bringing three days of blistering action, across 16 divisions, with upwards of 350 race cars competing.
As well as that oval there’s also a road racing course here, 1.7 miles long and rebuilt in 2014. Check out the track’s schedule for an opportunity to drive on this course with the likes of Lock City Drift and the SCCA Novice Permit School.
13. Point Breeze
This combined restaurant, entertainment venue and events facility at the tip of a peninsula on Webster Lake goes back as far as 1881 when it was established as a private men’s sailing club.
Point Breeze was an entertainment hotspot for Worcester County, and the destination of choice for businesses in the region making summer outings. The present owners took over in the 1980s, and have helped this historic establishment move with the times.
The tradition of live music continues to this day, and in terms of cuisine you’ve got tried-and-tested New England seafood faves like lobster rolls, fish & chips, clam chowder and baked haddock. The view from the deck is sublime, particularly at sunset.
14. Quaddick State Park
In Webster you’re spoiled for outdoor recreation options, as there’s an adjoining state park and state forest a little way over the line in Connecticut.
These are on the shores of the 466-acre Quaddick Reservoir, made up of lower, middle and upper sections, and originating with the construction of a dam on the Five Mile River in the 1860s.
Long before, this was a fishing area for the Nipmuck Native Americans, and is now a big draw for families in summer.
At Quaddick State Park you’ve got yet another swimming area to choose from, with a large sandy beach, boat launch, picnic area and grills. The water is perfectly clear in some places, and you can fish for crappie and pumpkinseed.
15. Advanced Action Sports
This outdoor airsoft and paintball center sits just off I-395 in the north of Webster. The playing field at Advanced Action Sports has been designed to resemble famous video game franchises, in an urban environment with a lot of opportunities for close-quarters battle.
A variety of interesting game modes and mission objectives are on offer to mix things up. Sessions are available Wednesday, Saturday and Sunday, and there’s a discount for booking online.
Also on site is a 5,000-square-foot store, stocked with all of the gear and accessories you could possibly need.