Trips & Routes

Small Towns

Trips & Routes
Small Towns

This Little-Known Waterfront Village Is One of the Most Charming in Massachusetts

While everyone else is stuck in Cape Cod traffic, you could be strolling past 19th-century mansions and eating world-class seafood in this quiet, whimsical waterfront village.

by Jasmine Vieau
on Apr 14
Onset Beach in Wareham, Massachusetts with sweeping waterfront views toward the pier and village.
Trips & Routes

Why Travelers Are Falling for This Small Historic Town in Massachusetts

by Kim Falchek
on Mar 28
An exterior view of the historic Burnham house in Essex, MA reflecting in the water.
Trips & Routes

The Historic Massachusetts Town Locals Hope Stays Off Tourists’ Radar

by Raymond Goldfield
on Mar 12
A close-up of an old mill at a historic ironworks in Saugus, MA.
Trips & Routes

5 Small Towns in Massachusetts So Dreamy, You’ll Swear You’ve Seen Them on TV

by Charlie Boyle
on Jan 21
A calm, wide river cuts in between green farmland dotted with small buildings at dusk. The river is lined with trees changing for fall and mountains loom large in the distance.
Trips & Routes

The Small Town in Massachusetts That Feels Straight Out of Hocus Pocus

by Jasmine Vieau
on Sep 22
A house decorated for Halloween in Salem with bright green and purple lights, skeletons, and pumpkins.

Latest Small Towns

Trips & Routes
Small Towns

The Remote Town in Massachusetts We Simply Can’t Get Enough Of

Tucked away in the Berkshires, Williamstown is the one remote town in Massachusetts that everyone should visit.

by Jackie Sutherlin
on Apr 9
A gravel path leads through a field with mountains in the distance.
Trips & Routes
Small Towns

Why Wareham, Massachusetts, the Gateway to Cape Cod, Is Worth a Visit in Its Own Right

Want to experience the magic of Cape Cod without the traffic? A trip to Wareham, Massachusetts is just as fun.

by Kim Falchek
on Jun 23
An ariel view of the Weweantic River in Wareham, Massachusetts. There are several boats in the water.
Trips & Routes
Small Towns

The Walkable Massachusetts Town That’s Known for Its Historic Charm

Hudson is a walkable town in Massachusetts known for its historic charm and vibrant food scene. Explore its award-winning Main Street, top-rated restaurants, and local breweries.

by Jasmine Vieau
on Dec 29
: An aerial view of a snowy town center featuring a traffic roundabout and historic brick buildings.
Trips & Routes
Day Trips
Small Towns

If You Only Have One Day to Visit This Small Town in Massachusetts, Here’s Everything You Absolutely Can’t Miss

Escape to Brewster, a small town in Massachusetts, for a perfect Cape Cod getaway. Explore nature, history, and local culture in this charming seaside town.

by Jasmine Vieau
on Nov 17
aerial shot of the brewster tidal flats, a mile of sand that appears during low tide on cape cod
Trips & Routes
Small Towns

This Blink-And-You’ll-Miss-It Town In Massachusetts Is So Worth Exploring

by Kim Falchek
on Aug 6
A large white two-story house with a gray roof, surrounded by greenery and a white picket fence.
Trips & Routes
Small Towns

The Cozy Small Town In Massachusetts That Comes Alive Under A Blanket Of Snow

by Kim Falchek
on Jan 8
A snowy scene featuring a clock tower surrounded by trees covered in fresh snow.
Trips & Routes
Small Towns

This Charming Community Is One Of The Most Peaceful Places To Live In Massachusetts

by Kim Falchek
on Nov 24
A rocky trail surrounded by lush green trees and foliage in a serene forest setting.
Trips & Routes
Small Towns

Most People Don’t Know That This Charming Small Town Inherited One Man’s Odd Name

by Andrea Verschuyl
on Nov 3
A park scene featuring a soldier monument, American flag, and trees under a clear blue sky.
Trips & Routes
Small Towns

The Most Remote Small Town in Massachusetts Is the Perfect Place to Get Away From It All

This remote town of Mount Washington is a peaceful getaway destination in Massachusetts.

by Kim Falchek
on Oct 18
exterior of a charming green and white church in the remote town of mount washington ma
Trips & Routes
Small Towns

The Small Town In Massachusetts That Comes Alive In The Fall Season

by Kim Falchek
on Sep 26
A scenic view of a lake surrounded by vibrant autumn foliage and rolling hills under a partly cloudy sky.
Trips & Routes
Small Towns

Enjoy The Simple Life When You Visit This Tiny Rural Community In Massachusetts

by Kim Falchek
on Sep 5
A wooden covered bridge spans a calm river, surrounded by trees and cloudy skies.
Trips & Routes
Small Towns

The Most Charming College Town In Massachusetts Is Home To Delicious Dining, Shopping, And More

Amherst is a vibrant New England college town known for its rich history, outdoor spaces, and cultural attractions.

by Kim Falchek
on Sep 1
A brick building with a clock tower, surrounded by green trees and a clear blue sky.
Trips & Routes
Small Towns

The Charming Small Town in Massachusetts That’s Perfect For A Fall Day Trip

Ipswich, Massachusetts offers a variety of fall activities including historic tours, apple picking, farm events, and scenic views.

by Kim Falchek
on Aug 8
A large white historic house with black shutters, surrounded by autumn trees, along a quiet road.
Trips & Routes
Small Towns

There’s No Community In Massachusetts More Enchanting And Historic Than Marblehead

Marblehead, Massachusetts, offers a charming and historical experience with its historic homes, museums, parks, and scenic views.

by Kim Falchek
on Jul 28
Charming street lined with historic homes, featuring white facades, black shutters, and colorful flower boxes.
Trips & Routes
Small Towns

The Kielbasa Capital Of Massachusetts Is One Of The Most Delicious Small Towns You’ll Ever Visit

Chicopee, Massachusetts, known as the "kielbasa capital," offers a variety of places to enjoy authentic Polish kielbasa and other traditional foods.

by Kim Falchek
on Jun 12
Historic brick building with a sign reading "Polish Center," surrounded by green lawn and a tent for events.
Trips & Routes
Small Towns

You’d Be Surprised To Learn That Hadley, Massachusetts Is One Of The Country’s Best Small Towns

Hadley, Massachusetts is a charming small town known for its beautiful scenery, outdoor activities, and welcoming vibe.

by Kim Falchek
on Jun 9
A scenic view of rolling hills, a river, and farmland under a partly cloudy sky.
Trips & Routes
Small Towns

Visit The Small Town Of Manchester By The Sea In Massachusetts, The Place That Inspired The Movie By The Same Name

Manchester-By-The-Sea, a picturesque coastal town in Massachusetts, served as a filming location for the award-winning movie "Manchester By The Sea."

by Kim Falchek
on May 31
A scenic harbor with several boats anchored, surrounded by buildings and trees under a partly cloudy sky.
Trips & Routes
Small Towns

There Might Be More Parks Than Stoplights In The Charming Town Of Topsfield, Massachusetts

Topsfield, Massachusetts, offers numerous parks and outdoor activities, making it a great destination for nature lovers.

by Melissa Mahoney
on May 1
A serene pond surrounded by lush greenery and lily pads under a clear blue sky.
Trips & Routes
Small Towns

With An Old-School Fudge Shop, A Public Fountain, And Cobblestone Streets, A Visit To Nantucket, Massachusetts Is A Delightful Step Back In Time

Nantucket, Massachusetts, is a charming island known for its historic buildings, cobblestone streets, and serene beauty.

by Melissa Mahoney
on Apr 4
A historic brick building with an American flag, surrounded by trees and a cobblestone street at sunset.
Trips & Routes
Small Towns

The Fascinating Town In Massachusetts That Is Straight Out Of A Fairy Tale

Tyringham, Massachusetts, is a picturesque town with historic sites, natural beauty, and unique attractions that resemble a fairytale setting.

by Melissa Mahoney
on Mar 24
A serene autumn landscape featuring colorful trees, a misty background, and a quaint village with a church.
Trips & Routes
Small Towns

The Most Criminally Overlooked Town In Massachusetts And Why You Need To Visit

Montague, Massachusetts is a charming town known for its scenic beauty, quirky attractions, and the famous Montague Bookmill.

by Sophia Mitrokostas
on Mar 24
alt
Trips & Routes
Small Towns

The Quiet Fishing Town In Massachusetts That Seems Frozen In Time

Rockport, Massachusetts, offers a blend of coastal charm and an inspiring art colony with scenic harbors and fresh seafood.

by Sophia Mitrokostas
on Mar 23
alt
Trips & Routes
Small Towns

Known As A Preserve America Community, The Small Town Of Sutton, Massachusetts Is Surrounded By Natural Beauty

Sutton, a small town in Massachusetts, offers picturesque natural beauty and historic sites worth exploring.

by Melissa Mahoney
on Mar 20
A quaint yellow house surrounded by trees, situated at the intersection of two roads on a sunny day.
Trips & Routes
Small Towns

Few People Realize How Much History Is Preserved In The Small Town Of Egremont, Massachusetts

Egremont, MA is a small town known for its well-preserved historical buildings and rural charm.

by Melissa Mahoney
on Jun 5
Sign marking the entrance to No. Egremont Village, a National Register Historic District, alongside a rural road.
Trips & Routes
Small Towns

This Tiny Town In Massachusetts Has A Little Bit Of Everything

by Sophia Mitrokostas
on Mar 22
alt
Trips & Routes
Small Towns

Almost Nobody Knows That Parts Of The Iconic Movie The Crucible Were Filmed In This Tiny Massachusetts Town

The Crucible was filmed on Choate Island in Essex, Massachusetts, known for its historic structures and unspoiled landscape.

by Melissa Mahoney
on Apr 12
A historic wooden house beside a calm waterway, surrounded by green fields and a clear blue sky.
Trips & Routes
Small Towns

The Surprising Massachusetts Town That Makes An Excellent Weekend Getaway

Petersham, Massachusetts offers a perfect weekend getaway with its nature trails, historic district, and charming local dining options.

by Melissa Mahoney
on Jul 6
Historic white building with a clock tower, surrounded by trees and a red brick structure, under a blue sky.
Trips & Routes
Small Towns

This Historic Massachusetts Town Is Worth a Day Trip

Plymouth, Massachusetts, offers a rich historical experience with numerous sites dating back to the Pilgrims' arrival in 1620.

by Melissa Mahoney
on Jun 9
Aerial view of downtown Plymouth, MA, showing historic architecture, a church spire, and boats in the harbor.
Trips & Routes
Small Towns

The Perfect Wellfleet Day Trip Itinerary – Not Your Average Bucket List Episode 8

Wellfleet, Massachusetts, is a popular summer destination known for its oysters and beach scene.

by Marisa Roman
on Feb 23
Panoramic view of a sandy beach with dunes, under a bright blue sky with wispy clouds and calm ocean waves.
Trips & Routes
Small Towns

The Ancient Town In Massachusetts That’s Loaded With Fascinating History

Gloucester, Massachusetts, is a historic coastal city with numerous attractions, including beaches, whale-watching, and historic sites.

by Sophia Mitrokostas
on Feb 10
A stone building with towers and arches, surrounded by trees and greenery, creating a serene, historic atmosphere.
Trips & Routes
Small Towns

There’s A Little Town Hidden In The Massachusetts Mountains And It’s The Perfect Place To Relax

Lee, a charming mountain town in the Berkshires, Massachusetts, offers a relaxing getaway with historic sites, boutiques, and scenic nature trails.

by Melissa Mahoney
on Jan 20
A charming storefront with large windows displaying colorful flowers and plants, set along a tree-lined sidewalk.
Trips & Routes
Small Towns

This Charming Little Farm Town In Massachusetts Is The Perfect Place To Get Away From It All

Heath, a rural town in Massachusetts, offers natural beauty, historic buildings, and a peaceful community atmosphere.

by Melissa Mahoney
on Jan 12
A serene waterfall cascades over a stone wall, surrounded by autumn foliage and a tranquil pond.
Trips & Routes
Small Towns

Few People Know This Charming Small Town In The Geographic Center Of Massachusetts

Rutland, a charming small town in Worcester County, is the geographic center of Massachusetts with several must-see locations.

by Melissa Mahoney
on Nov 17
Sign for Rutland State Park beside a calm lake, surrounded by tall trees and greenery.
Trips & Routes
Small Towns

The 300-Year-Old Curse That Still Plagues This Seaside Town In Massachusetts

Salem, Massachusetts, is known for its ghost stories, including the legend of Giles Corey and his curse on the town's sheriffs.

by Sophia Mitrokostas
on Jan 4
A cloudy day at a harbor featuring a historic building and a tall ship docked nearby.
Trips & Routes
Small Towns

The Unassuming Town Of Salisbury, Massachusetts Is One Of America’s Best Hidden Gems For A Weekend Getaway

Salisbury Beach in Massachusetts offers a perfect weekend getaway with its pristine beaches, outdoor activities, and unique dining experiences.

by Melissa Mahoney
on Jan 15
A serene beach scene with gentle waves, sandy shore, and distant buildings under a clear blue sky.
Trips & Routes
Small Towns

This Tiny Massachusetts Town Is The Grandest Winter Wonderland You’ll Ever Visit

Concord, Massachusetts transforms into a magical winter wonderland with historical sites and natural beauty.

by Melissa Mahoney
on Nov 17
A snowy landscape featuring a church with a tall steeple, surrounded by snow-covered trees and a clear blue sky.
Trips & Routes
Small Towns

Visit These 12 Incredible Charming Small Towns in Massachusetts, One for Each Month of the Year

Discover 12 charming small towns in Massachusetts, each offering unique attractions and activities for every month of the year.

by Melissa Mahoney
on Jan 6
alt
Trips & Routes
Small Towns

This Enchanting Town In Massachusetts Is Unlike Any Other In The World

by Melissa Mahoney
on Nov 21
A serene harbor scene with boats, colorful buildings, and a church steeple reflected in calm water under a cloudy sky.
Trips & Routes
Small Towns

Here Are The 10 Richest Cities In Massachusetts

Lists the wealthiest cities in Massachusetts based on median income, poverty levels, and unemployment rates.

by Sophia Mitrokostas
on Dec 25
alt
Trips & Routes
Small Towns

We Bet You Didn’t Know This Small Town In Massachusetts Was Home To The Oldest Grape Juice Company In America

Concord, founded in 1635, is home to the oldest grape juice company in the world, Welch's, and has a rich historical significance.

by Melissa Mahoney
on Dec 16
A metal basket filled with grapes next to a bottle of Welch's grape juice, with purple rain boots in the background.
Trips & Routes
Small Towns

The Historic Town In Massachusetts That Comes Alive During The Winter Season

North Adams, Massachusetts, is a popular winter destination known for its proximity to ski resorts, Mass MoCA, and seasonal events like WinterFest.

by Melissa Mahoney
on Jan 19
Snow-covered town with buildings and a mountain in the background, under a cloudy sky. Traffic lights visible.
Trips & Routes
Small Towns

The Charming Small Town In Massachusetts Where You Can Still Experience An Old-Fashioned Christmas

Old Sturbridge Village in Massachusetts offers an old-fashioned Christmas experience with its annual Christmas by Candlelight festivities.

by Melissa Mahoney
on Nov 30
A snowy landscape with rustic buildings and a glowing lantern, surrounded by trees under a cloudy sky.
Trips & Routes
Small Towns

This Massachusetts Christmas Town is Straight Out of a Norman Rockwell Painting

Stockbridge, Massachusetts, is famous for being depicted in Norman Rockwell's painting and hosts an annual Christmas celebration.

by Melissa Mahoney
on Oct 18
main street stockbridge massachusetts all decked out for christmas
Trips & Routes
Small Towns

Here Are The 7 Coolest Small Towns In Massachusetts You’ve Probably Never Heard Of

Explore some of the coolest small towns in Massachusetts, each with its own unique charm and attractions.

by Melissa Mahoney
on Nov 9
A quiet street lined with charming houses, featuring a distinctive yellow building with a tower and trees along the sidewalk.
Trips & Routes
Small Towns

Massachusetts’ Charming Town Of Stockbridge Was Named The Best Christmas Town In America

Stockbridge, Massachusetts is celebrated as the top Christmas town in the U.S. for its festive decorations and holiday events.

by E Jamar
on Oct 20
A festive street scene with people gathered near historic buildings and vintage cars, decorated for the winter season.
Trips & Routes
Small Towns

Here Are The 7 Most Enchanting, Magical Christmas Towns Around Boston

Discover the best Christmas towns in Massachusetts, each offering unique holiday festivities and charm.

by Juliet White
on Nov 4
A beautifully lit greenhouse at night, with a fountain and a turtle statue in a pond, surrounded by festive decorations.
Trips & Routes
Small Towns

Discover the Massachusetts Main Street That’s Downright Enchanting at Christmas

Newburyport, Massachusetts, offers enchanting Christmas events and decorations, making it a must-visit holiday destination.

by Sophia Mitrokostas
on Oct 23
snow falls over downtown newburyport massachusetts at night
Trips & Routes
Small Towns

These 7 Small Towns In Massachusetts Honor Christmas In The Most Magical Way

Discover the best Christmas towns in Massachusetts, each offering unique holiday events and festive activities.

by Melissa Mahoney
on Oct 31
A festive inn decorated with wreaths and lights, featuring a porch and an American flag, set in a cozy evening atmosphere.
Trips & Routes
Small Towns

Massachusetts Just Wouldn’t Be The Same Without These 7 Charming Small Towns

Explore seven charming small towns in Massachusetts that have significantly shaped the state's character and offer unique attractions.

by Melissa Mahoney
on Oct 21
Colorful houses line a calm harbor, reflecting in the water under a clear sky. Boats are moored nearby.
Trips & Routes
Small Towns

The 12 Most Magical Christmas Towns in Massachusetts

Discover the best Christmas towns in Massachusetts, each offering unique holiday events and festive activities.

by Sophia Mitrokostas
on Nov 11
Sunset photo of the Nantucket Lighthouse with a Christmas wreath on the side