These Massachusetts Lake Towns In The Berkshires Are Taken Over By Fall Crowds
Every fall, several Berkshire lakes get partly drained on purpose, right when the leaves hit peak color. It’s called a drawdown, and one lake on this list starts lowering its water in mid-October like clockwork.
Another lake here was built in 1865 by damming a river named, of all things, the Fall River. I love that detail.
It feels like the region planned its autumn branding over 150 years ago.
Western Massachusetts towns pair those shorelines with pumpkin shows, mountain lodges, and rail trails that hug the water. Leaf peepers figured this out long ago, and they keep showing up with cameras ready.
So which lake towns turn into autumn headquarters each September and October? Honestly, I can’t think of a better excuse to grab a jacket, pack a snack, and chase red and gold leaves reflected in still water.
1. Stockbridge
Over 1,500 jack-o’-lanterns light up a single garden here each October, which is a lot of carving for one town. The Incredible Naumkeag Pumpkin Show runs Wednesday through Sunday through October 31, and timed tickets are required in advance.
Grab some hot cider and a fall treat while you wander past mums and gourds. The famous Blue Steps and Monument Mountain views make the backdrop hard to beat.
Then there’s the water. Stockbridge Bowl, once known as Lake Mahkeenac, stretches 1.7 miles and reaches 48 feet at its deepest point.
Paddlers can explore about six miles of shoreline across 372 acres. Kwuniikwat Island even offers public picnic tables and a dock, so pack a sandwich.
No kayak? The Stockbridge Library lends them out, which might be the best library card perk in Massachusetts.
Back in town, the Norman Rockwell Museum houses the artist’s studio and a big collection of American illustration. Main Street, lined with boutiques and galleries, looks like it hopped right off one of his canvases.
Want shade and a little drama? Ice Glen, a glacial ravine in the town’s southeast corner, holds old-growth pine and hemlock that keep the trail cool.
History fans, take note. British missionaries settled Stockbridge in 1734, and the town was incorporated in 1739 as a community for the Stockbridge Mohican people.
Finish with a rocking chair on the Red Lion Inn’s front porch. Watching leaves drift down Main Street counts as an official activity, right?
2. Lee
Hop off the Massachusetts Turnpike, and Lee is often the first town to say hello. No wonder it goes by the nickname Gateway to the Berkshires.
That title comes with real perks for leaf peepers. You can trade highway lanes for hillside color in just a few minutes.
Laurel Lake is the star of the show here. The water is known for being clear, and the shoreline makes a lovely place to pause.
Pack a light jacket and plan a short hike nearby. Then head back to the water to watch the trees reflect red and orange across the surface.
Anglers can bring a rod and spend a calm morning hoping for a bite. Paddlers will find plenty of room to glide and gawk at the hills.
Downtown has its own appeal. A traditional brick-front Main Street gives the town a classic New England look that photographs beautifully in autumn light.
Lee also has deep paper-mill roots. The Housatonic River runs through town, adding another scenic stretch to explore.
With roughly 5,700 residents, the town feels lively without losing its small-town character. Stroll the sidewalks, peek into shop windows, and grab a snack for the road.
From here, the surrounding Berkshire hilltops are easy to reach. Tour groups and foliage chasers use Lee as a launch pad, and it’s easy to see why.
Tip for your trip: start early and leave room for detours. A spontaneous lakeside stop might become the best part of your day.
3. Otis
A river called the Fall River got dammed in 1865, and the result steals the show each autumn. Otis Reservoir is the largest body of water in the Berkshires, with a 15-mile perimeter to explore.
Covering more than 1,000 acres, the reservoir borders Tolland State Forest. Kayaks, canoes, and fishing rods feel right at home here.
Anglers can chase trout, bass, pickerel, perch, and bullhead. A public boat ramp sits inside the state forest, and there’s a car-top launch near the dam.
Fun fact: the reservoir goes through an annual drawdown in fall and winter. October water levels may differ from summer, which is handy to know before launching.
Need more water? Big Benton Pond covers 327 acres and gets stocked with rainbow, brook, and brown trout each year.
On land, Tolland State Forest offers hiking, biking, and the self-guided Gilmore interpretive trail. Its campground is open seasonally from late spring into fall, and reservations are required.
Hungry after a day of fresh air? Otis Ridge Ski Area, running since 1946, opens its Grouse House restaurant in the fall from Thursday through Sunday.
Craving a country store stop? Otis Poultry Farm sells pies, cheese, fresh eggs, and even sheepskin slippers.
History buffs will enjoy this one. Colonel Henry Knox passed through town in January 1776 along what’s now the Knox Trail.
Snap a photo of the reservoir at sunset before heading home. Your camera roll will thank you later.
4. Monterey
Only about 1,100 people call Monterey home, yet the town packs in two lakes and a giant forest. That’s a pretty impressive ratio of trees to neighbors.
Lake Garfield covers more than 250 acres and averages about 16 feet deep. A public boat launch sits on Tyringham Road, just south of the town beach.
Bring a rod for bass, bluegill, perch, or stocked trout. Lake Buel, another Great Pond, gives you a second shoreline to admire.
Route 23 turns into a leaf-peeping corridor in fall. It’s a slower country drive, which makes it perfect for pulling over to snap lake reflections.
Ready to stretch your legs? Beartown State Forest spans over 12,000 acres, including almost six miles of the Appalachian Trail.
Keep your eyes open for deer, and maybe even a bobcat. Benedict Pond sits inside the forest and makes a great turnaround point.
History waits nearby at the Bidwell House Museum, a Georgian saltbox built around 1760. Guided tours run by appointment through October, while the grounds stay open year-round.
Its 194 acres include six miles of trails. One of them is a Native American Interpretive Trail, adding meaning to your walk.
Breakfast is covered too. The Roadside Cafe and Store, run by Gould Farm, serves home-style breakfast and lunch Wednesday through Sunday.
Monterey split off from Tyringham and became its own town in 1847. Not bad for a place that still feels refreshingly unhurried.
5. Richmond
Iron ore turned up in Richmond in 1829, but these days the town’s real treasures are fruit and water. Orchards and open pastures roll right up to the New York border.
Richmond Pond is the headline here. It covers 218 acres and reaches 53 feet deep, fed by streams and springs.
Paddlers get a kayak launch dock beside the public boat ramp, which suits shallow-draft boats. Two accessible fishing platforms make it easy for anyone to cast a line.
What’s biting? Largemouth bass, rock bass, pickerel, perch, bluegill, and stocked trout call this pond home.
Some history lingers on the shore too. The pond’s oldest cabin dates to 1895, and Camp Russell started here as a boys’ camp in 1910.
Then comes the apple chapter. Farmstands and apple orchards like Bartlett’s Orchard give your fall drive a delicious detour.
Hilltop Orchards on Canaan Road adds another orchard to the map. It even hosts evening events in October, so check its calendar before you go.
Just over the line in Pittsfield, Hancock Shaker Village goes big for October. Its Halloween Pumpkin Extravaganza Family Day each October includes pumpkin decorating and a scavenger hunt.
Older kids can join special guided tours on select October evenings. Guided walks on the Farm and Forest Trail are calmer, but just as scenic.
Founded by settlers in 1759 and incorporated in 1765, Richmond wears its age gracefully. Bring your camera to the pond at golden hour and let the colors do the work.
6. Cheshire
Back in 1800, Cheshire was the only Berkshire town to favor Thomas Jefferson for president. Clearly, this place has always marched to its own beat.
Today, that independent streak shows up on the water. Cheshire Reservoir, also called Hoosac Lake, is a shallow lake framed by mountain ridges.
Kayaks and canoes glide easily across its surface, and some areas allow motorboats. Picnic tables wait nearby for your lakeside lunch break, so pack sandwiches.
Now let’s talk wheels. The Ashuwillticook Rail Trail is a 10-foot-wide paved path built on an old railroad bed, running right along the reservoir.
Bikes, rollerblades, and running shoes are welcome. Views stretch across the water toward Mount Greylock, which turns red and gold each autumn.
Farnum’s Causeway is a favorite spot for casting a line. Largemouth bass, yellow perch, and stocked trout swim in these waters.
Want a bigger challenge? About six miles of the Appalachian Trail pass through Cheshire, including the Father Tom Campsite.
The Cheshire Harbor Trail, starting in nearby Adams, is known as the most gradual climb to Greylock’s summit. Your legs will appreciate that kindness.
Save room for a sweet finish at Whitney’s Farm Market. It’s known for apple cider donuts, plus pumpkins, goats, and a playground in fall.
Fun history bit: the reservoir dam was completed in 1870. Rhode Island Baptists founded the town, so this lakeside spot has a long, proud, and quirky backstory.
7. Lenox
Around here, the word cottage gets used very loosely. The town’s Gilded Age summer cottages are actually grand mansions, and you can tour one in person.
Ventfort Hall, a Jacobean Revival mansion built in 1893, now houses The Museum of the Gilded Age. Self-guided tours run daily, and fall brings seasonal events to the mansion.
Prefer something cozy? The mansion also hosts Tea and Talks, which sounds lovely for a chilly afternoon.
Now for the lakes. Lenox shares Laurel Lake, a calm spot to fish, kayak, paddleboard, or jet ski when the weather cooperates.
The town also borders the northern reach of Stockbridge Bowl. That means two lakes for foliage photos in one quick trip.
Music lovers know Tanglewood as the summer home of the Boston Symphony Orchestra since 1937. Its grounds cover more than 400 acres, and fall programs pop up in Studio E at the Linde Center.
Out on the trails, Pleasant Valley Sanctuary puts on a serious color show across its hillsides. Bring good shoes and maybe an extra camera battery.
Harvest events at The Mount add another reason to linger. History and crisp autumn air make a pretty great team.
Afterward, stroll the walkable village center, home to around 5,000 residents. Window shopping in a sweater is basically required in Massachusetts this time of year, and nobody will judge your scarf collection.
8. Lanesborough
A 30-foot boulder balanced on its tip sounds like a cartoon prop, yet you can see one in Lanesborough. Balance Rock State Park shows off this glacial erratic at the north end of Pittsfield State Forest.
Down by the water, Pontoosuc Lake stretches 511 acres between Lanesborough and Pittsfield. Northern pike swim here, and boat rentals make it easy to get out on the lake.
Paddleboarders and kayakers can soak up lakeside foliage views. The annual drawdown starts in mid-October, so plan your paddle with that in mind.
Then look up. Mount Greylock, the highest peak in Massachusetts at 3,491 feet, rises just to the north.
On clear days, the summit shows off views across five states. The Veterans War Memorial Tower stays open through Indigenous Peoples Day.
Up top, Bascom Lodge was built by the Civilian Conservation Corps in the 1930s. Its dining room has a fireplace, and lunch runs until 4:30 p.m.
Overnight stays continue through October 31. Waking up above the treetops, then heading in for breakfast, sounds like a fine fall plan.
Prefer flat ground? The main entrance to the Ashuwillticook Rail Trail sits right here in town.
Lanesborough dates to 1765 and takes its name from the Countess of Lanesborough. Humorist Josh Billings, born Henry Wheeler Shaw, ranks among its famous sons.
The summit tower is open seasonally, so check its schedule before you go. You’ll find it at 30 Rockwell Road, Lanesborough, MA 01237, so point your car uphill.