Norman Rockwell painted Stockbridge so often that the real Main Street now looks like one of his canvases come to life. That is the trick these Massachusetts towns pull off. A whaling-era cobblestone lane on Nantucket and a Revolutionary common in Concord do the same thing in different accents. Each one packs its best landmarks into a few blocks you can cover on foot. The eight New England streets here all sit under 50,000 residents and earn their reputation the honest way.

Stockbridge

Fewer than 2,000 people live in Stockbridge, yet its Main Street may be the most recognizable in the state. Credit Norman Rockwell, who lived here and painted the view down the street so many times it lodged in the national memory. The white clapboard buildings, the old inns, and the big shade trees are all still right where he left them, and people still use them.

The Red Lion Inn has welcomed guests on this corner since 1773, and its long front porch is the street’s anchor in every sense. A short walk away, the Norman Rockwell Museum holds the largest collection of his work and even his relocated studio. Naumkeag adds a Gilded Age cottage with terraced gardens climbing the hillside. Come December, the town recreates Rockwell’s famous “Main Street at Christmas” scene with vintage cars parked along the curb, which is about as close as a real place gets to stepping into a painting.

Lenox

Edith Wharton built her dream house just outside Lenox, and the writer’s eye for proportion seems to have rubbed off on the whole town. The center is small enough to park once and walk, with bookshops, cafes, and galleries shoulder to shoulder under the trees. Under 10,000 people live here, and the place wears its Berkshire elegance lightly.

The Mount, Wharton’s 1902 estate, runs as a house museum and public garden and hosts readings and outdoor events all summer. Ventfort Hall, a Jacobean-style mansion built for a sister of J.P. Morgan, fills in more of the Gilded Age story. Just up the road, Tanglewood draws crowds every July and August as the summer home of the Boston Symphony Orchestra, so a quiet shopping street can be ten minutes from a world-famous concert lawn. Few towns this size balance that kind of culture against that little traffic.

Concord

On April 19, 1775, the shot heard round the world was fired a short walk from where Concord shoppers now buy their morning coffee. That is the strange gift of this town. Its pretty village center sits below 20,000 residents, and its old houses, churches, and civic buildings look calm until you remember what happened among them.

Minute Man National Historical Park preserves the battle road and the fields where colonial militia turned back British regulars. Old North Bridge marks the spot itself, with Daniel Chester French’s Minute Man statue standing guard. Concord also raised more than its share of writers, and Louisa May Alcott’s Orchard House, where she wrote “Little Women,” still opens for tours. Two miles south, Walden Pond holds the woods Thoreau made famous, an easy swim or walk that closes the loop between the town’s history and its quieter ideas.

Marblehead

The streets in Marblehead’s Old Town were laid out for foot traffic and fishing nets, not cars, so they bend and narrow and dead-end at the water. The town tops 20,000 residents now, but the historic core feels far older and more intimate. Washington Street and the lanes around it run past brick sidewalks and preserved houses, with the harbor flashing into view between rooftops.

The Jeremiah Lee Mansion, a grand Georgian house built in 1768 for the wealthiest merchant in colonial Massachusetts, still keeps its original hand-painted English wallpaper. Old Burial Hill rises above town with weathered colonial gravestones and one of the best harbor views around. Abbot Hall, the brick town hall with the clock tower, houses the original “Spirit of ’76” painting. Walk the waterfront and the reason for the whole town becomes obvious. Marblehead grew up facing the sea, and it never turned away.

Newburyport

Federal-era sea captains built their fortunes at the mouth of the Merrimack, and their three-story brick blocks still line the streets of downtown Newburyport. The Main Street feeling here spreads across several streets rather than one. Under 20,000 residents keep the center humming, with shops and restaurants filling old facades right down to the riverbank.

Market Square and State Street form the heart of it, a tight grid of brick that survived a great fire and a wave of 1970s urban renewal to come out the other side intact. The Custom House Maritime Museum, set in a granite 1835 building, tells the port’s seafaring story. Waterfront Park gives you a bench and a view of the boats. A few miles out on Plum Island, the Parker River refuge at Joppa Flats turns the same trip into prime birdwatching, so a downtown afternoon can end with herons instead of storefronts.

Rockport

A plain red fishing shack on a granite pier may be the most painted building in America, and it sits right in Rockport’s harbor. Locals call it Motif No. 1, after an art teacher who got tired of seeing his students paint it. The town runs under 10,000 residents and folds its best parts into a few tight blocks by the water.

Main Street leads to Bearskin Neck, a skinny peninsula crammed with galleries, candy shops, and lobster shacks that ends with the open Atlantic. Front Beach puts sand and water within a short stroll of the shops. The Shalin Liu Performance Center, opened in 2010, built a concert hall with a wall of glass behind the stage, so the ocean becomes the backdrop for a string quartet. You can wander from a storefront to a harbor view to a gallery without ever breaking stride.

Great Barrington

Great Barrington wired the first downtown in the world lit entirely by alternating current, back in 1886, and the place has kept that forward lean ever since. Under 10,000 residents fill a center that feels genuinely busy, with restaurants, bookstores, and galleries spread along Main Street and Railroad Street. It looks like an old Berkshire town and behaves like a young one.

The Mahaiwe Performing Arts Center, a restored 1905 theater, books films, concerts, and live broadcasts year-round. The Housatonic River Walk threads a half-mile greenway along the water right behind Main Street, the work of volunteers who spent decades clearing a once-polluted bank. Just outside town, Monument Mountain offers a short climb to a quartzite ridge and a long view over the Housatonic River valley, the same trail Herman Melville and Nathaniel Hawthorne hiked together in 1850.

Nantucket

Whaling money built Nantucket’s Main Street, and the cobblestones laid to keep wagon wheels out of the mud are still there to rattle your suitcase. The island stays well under 50,000 year-round residents even at the height of summer. Brick sidewalks, weathered shingles, and window boxes give the downtown the texture of an old port rather than a new outdoor mall.

The Whaling Museum, set in an 1847 candle factory, explains how a small island once lit the lamps of the world, right down to a full sperm whale skeleton. Brant Point Lighthouse marks the harbor entrance and ranks among the most photographed beacons in New England. Straight Wharf keeps the working waterfront within steps of the shops, and the Oldest House, built in 1686, anchors the streetscape in the island’s first century. Every detail down to the gray shingles seems to point back to the same seafaring story.

Massachusetts Main Streets Worth Slowing Down For

What ties these eight together is not a shared look but a shared honesty. Stockbridge and Lenox lean on Berkshire culture, Concord carries the weight of 1775, and Great Barrington keeps reinventing itself. Marblehead, Newburyport, Rockport, and Nantucket all grew up facing salt water and never lost the habit. The best Main Streets here are not stage sets. They are working downtowns that happen to be worth a long, slow look.

No single person in Massachusetts bears more responsibility for denying voters the right to cast a ballot than inept Attorney General Andrea Campbell.

No rent control? Blame Campbell.

No state income tax cut? Blame Campbell.

No audit of the state Legislature? Blame Campbell.

Again and again Campbell has screwed up or worse, been complicit, leaving Bay State voters without the ability to exercise their right to decide important issues.

No amount of fawning pieces in the Boston Globe or publicity-seeking lawsuits against President Trump can cover up that fact.

She is a disaster. Unfortunately we have to suffer through another four years of her bonehead decision-making because Republicans in Massachusetts are just as inept at fielding viable candidates.

Massachusetts voters had the best chance in two decades this fall to establish rent control with a referendum question capping rent increases at 5%. Polls showed the ballot question with a solid advantage.

But Campbell, a liberal Democrat, allowed language on the question giving exemptions from the rent limits to religious institutions, which in Massachusetts violates the Constitution. The Supreme Judicial Court voted unanimously to kick the referendum question off the ballot.

This was not a case of political decision-making on Campbell’s part, since Democrats favored the rent control question. It was purely a rookie botch job, and a huge one at that, which will have major ramifications for renters, who will now be denied a much needed break from astronomical increases.

A simple reading of the Constitution should have caused Campbell to flag the question, and get the rent control advocates to strike the religious exemption. She admitted after she “got it wrong” — which is of no help to the renters in this state.

Apparently following the law, as Martin Short’s synchronized swimmer character would say, is not the Attorney General’s strong suit.

A similar error — or possibly an insidious political move — on Campbell’s part also blocked voters from getting a chance at lowering the state income tax from 5% to 4%.

The referendum question clearly had majority support, but was strongly opposed by Democrats like Campbell who argued it would have led to unconscionable cuts in social service programs to make up for the lost tax revenue.

Campbell okayed fatally flawed language in the ballot question which again caused the SJC to punt it off the ballot. This one may not have been just a simple mistake, but a possible deliberate act by Campbell to poison the question.

Politics again played a role in Campbell’s moves around a 72% voter-approved legislative audit by Auditor Diana DiZoglio. By not enforcing the new law, Campbell is flagrantly keeping DiZoglio from auditing the books of the despised, free-spending Legislature.

Campbell — rather than do her job — will not represent DiZoglio in her efforts to secure the audit, but authorized her to seek outside counsel, which will cost millions.

So on one hand saying she’ll enforce the law, she’s done everything she can to block it.

So what does Campbell do exactly? She has sued the Trump administration 50 times already, on a pace to exceed even Gov. Maura Healey’s lawsuits against Trump back when she was AG.

And she rarely ventures outside her Dartmouth, Mass. manse. Far from being the people’s lawyer, she stands against the people’s will.

Take the 1980s sitcom, “The Golden Girls.” The four older women sharing a home in that series formed close friendships. But homesharing — the practice of renting out a bedroom in one’s home — can also be a practical way to save money and take full advantage of a property.

Advocates seeking to promote homesharing estimate that leasing just 10 percent of the state’s 500,000 unoccupied spare bedrooms would be the equivalent of building $25 billion in new housing. And proponents, including community development financing organization BlueHub Capital, the Environmental League of Massachusetts, and Associated Industries of Massachusetts, are pushing for new laws that aim to turn homesharing from a niche practice into a genuine solution.

And amid burgeoning interest in homesharing, several companies have created platforms to facilitate it, like HomeShare Online, Nesterly, and SpareRoom. Some of these companies provide a website for potential roommates to find each other while others also offer background checks, personalized matching, help crafting legal agreements, and assistance navigating disputes.

Usually, homesharing involves sharing common areas in addition to having a private bedroom. Sometimes, a guest will exchange domestic tasks for reduced rent. A typical host might be an older adult who lives alone and wants help or extra income. A guest might be a student or single adult seeking inexpensive rent.

But sharing space with strangers can be tricky.

Honey Donegan, 77, who works part-time as a nanny, lives in a 2,500-square-foot home in Quechee, Vermont, and has turned to homesharing for companionship.

Her first guest didn’t work out — she was an older woman who ultimately decided to live with a family member. But then Donegan matched with Kayla Mazza, 31, through the nonprofit HomeShare Vermont. Mazza is a data and systems manager at a social services nonprofit who had trouble finding inexpensive housing near her job. They’ve lived together for two years. “It’s wonderful,” Donegan says. “It’s like having a daughter you’re not angry with.”

Most evenings, Donegan and Mazza watch “Jeopardy” together. They share a kitchen and occasionally a meal. Donegan loves hearing the younger woman’s perspective on work and politics. “We have separate lives, but we enjoy one another,” Donegan says.

Homeshare Vermont spokesperson Ric Cengeri said the organization conducts background checks, matches people by hand, negotiates contracts, and provides case management. At the moment, the program has matched around 300 people living in homesharing agreements, with the average match lasting 21 months.

One reason the Vermont program may have succeeded is that it is relatively small and has a human touch, with staff working closely with the host and guest to craft contracts and resolve disagreements. It’s also heavily subsidized with money from a state legislative appropriation through the Vermont Department of Disabilities, Aging and Independent Living, federal government matching funds, and foundation grants, so the fees are affordable: A one-time fee of between $60 and $500 when a match is made is applied on a sliding scale, based on income.

The Vermont program, modest as it is, suggests that homesharing could have a future. But the struggles of other pilots point to some of the model‘s limitations.

Although homesharing appeals to some, others worry about living with strangers. An older adult’s health needs can get in the way, if a host expects or needs more help than a guest is prepared to give. Sometimes, there are personality clashes.

Martha’s Vineyard might seem like a perfect place for homesharing. Cindy Trish, executive director of Healthy Aging Martha’s Vineyard, said the island is filled with older adults with large homes, while younger professionals can’t find housing. And in June 2022, Healthy Aging launched a homesharing pilot program.

The surprising conclusion: It wasn’t viable. Program staff interviewed 13 hosts and 30 guests and identified just four potential matches, who were referred to a mediation agency to negotiate agreements. Only one pair signed a contract.

Trish said hosts often had more home health care needs than guests could meet, and the accommodations frequently didn’t meet guests’ expectations.

Elsewhere, the state of Maine partnered with Nesterly on a two-year pilot program, which ended in early 2026. Erik Jorgensen, senior director of government relations at Maine State Housing Authority, said because the program was statewide and lacked sufficient marketing, it had trouble attracting a critical mass of guests and hosts in any one location. Jorgensen said more than 500 potential hosts and guests created profiles, but only 11 homeshares were actually booked.

Nesterly CEO Noelle Marcus said the organization continued making matches after the pilot ended and has made about three dozen matches altogether. She’s seeking funding from local organizations to continue the program.

Nesterly also ran a pilot program in Boston in 2017 under Mayor Marty Walsh, which was paused during COVID-19 and not renewed by Mayor Michelle Wu.

There is talk of some legal changes that might make homesharing more attractive — making it easier for landlords to evict lodgers, for instance. Financial incentives — either to incentivize homeowners to rent rooms or to cover administrative costs for homesharing organizations — could help, too.

Portland, Ore. just launched a 12-month pilot program giving grants to homeowners who rent out spare rooms. HomeShare Vermont relies, in part, on $318,000 in state grants to cover its overhead expenses.

But ultimately, it may be a different kind of homesharing that takes hold — one that caters to the instinct for privacy.

Massachusetts has had early success with new laws encouraging construction of accessory dwelling units (ADUs), small living units located on the same property as a single-family home. In 2025, around 1,200 new units were permitted, according to state data. For renters seeking private living units or seniors concerned about sharing common space, renting an ADU could provide privacy for both parties while still letting a guest swap some household tasks for a discount.

Homesharing, or really any attempt to squeeze more out of our existing properties — allowing for ADUs, rezoning single-family lots to allow two-family homes — will not completely solve Massachusetts’ housing crisis. Ultimately, we need to build more housing.

But done right, homesharing can contribute in a small way. And we could use any contribution we can get.

Shira Schoenberg can be reached at shira.schoenberg@globe.com. Follow her @shiraschoenberg.