Trips & Routes

Small Towns

Trips & Routes
Small Towns

This Little-Known Waterfront Town Is One of the Most Charming in Maryland

Located on the Choptank River, Cambridge is a little-known waterfront town in Maryland home to stunning lighthouses and historic streets.

by Raymond Goldfield
on Apr 13
The Choptank River Lighthouse in Cambridge, Maryland at night, illuminating the river.
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The Bayfront Maryland Town Locals Hope Stays Off Tourists’ Radar

by Raymond Goldfield
on Mar 10
A small town square with a town map reading "Leonardtown" and a cardboard cutout figure smiling next to it.
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5 Small Towns in Maryland So Dreamy, You’ll Swear You’ve Seen Them on TV

by Charlie Boyle
on Feb 1
An orange sunset glows over the outline of a coastal town with residences sitting right next to the water. The water remains still to a point of near perfect reflection.
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The Small Town in Maryland That Feels Straight Out Of ‘Wedding Crashers’

by Jacki Mick
on Dec 13
A bright sunset over the water, seen across the metal railing of what appears to be a bridge or causeway.
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Escape to This Charming Mountain Town in Maryland Before Fall Ends

by Melanie Johnson
on Sep 29
A historic covered bridge surrounded by fall foliage and a flowing creek in Thurmont, a mountain town in Maryland

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Small Towns

This Tiny Town in Maryland Feels Like a Living Time Capsule

With historic landmarks, a quaint district and quirky festivals, this tiny community in Maryland is frozen in time.

by Melanie Johnson
on Jan 9
exterior of st. bartholmew's church in laytonsville maryland
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Small Towns

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

Take in sparkling views of Chesapeake Bay, plenty of seafood, and a healthy dose of maritime history on this small island.

by Kate Kolenda
on Apr 3
Blue sky over a waterfront view from Solomons Island MD.
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Small Towns

Skip Europe This Summer: This Island in Maryland Is Just as Peaceful as the Wadden Islands in the Netherlands

Skip the flight to Europe—Smith Island in Maryland feels like the Wadden Islands in the Netherlands, with car-free streets, fresh seafood, and water views.

by Jasmine Vieau
on Jun 30
A vibrant sunset over the tidal marshes and winding creeks of Smith Island, with golden light reflecting on the water.
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Small Towns

The Walkable Maryland Town That’s Known for Its Waterfront Views

Stroll along Main Street in Annapolis, a charming, walkable town in Maryland, perfect for a day trip or a weekend getaway.

by Beth Price-Williams
on Dec 23
Strung lights illuminate a historic Annapolis street at night, viewed through an open iron gate framed by large trees.
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If You Only Have One Day to Visit This Small Town in Maryland, Here’s Everything You Absolutely Can’t Miss

Explore Emmitsburg, a small town in Maryland with historic sites, local dining, and hiking in Catoctin Mountain Park.

by Jasmine Vieau
on Nov 13
Dome of the Basilica at the National Shrine of Saint Elizabeth Ann Seton in Emmitsburg, Maryland
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Small Towns

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

Brimming with history, natural beauty, and charming locals, the small town of Chesapeake City, Maryland is worth a stop.

by Beth Copenhaver
on Nov 12
a canal-side restaurant with lawn seating and views of the cheasapeake city bridges in maryland on a sunny day
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Small Towns

The Small-Town Restaurant That Is Worth A Visit From Anywhere In Maryland

by Beth Copenhaver
on Jan 29
A colorful pub with outdoor seating on a sunny street, featuring a rooftop deck and trees nearby.
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Small Towns

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

by Courtnie Erickson
on Jan 10
A snowy landscape featuring a cluster of houses and trees, with a backdrop of a wintery town.
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Small Towns

Enjoy A Classical Christmas When You Visit This Charming Small Town In Maryland

by Beth Copenhaver
on Dec 15
A vintage red fire truck decorated with lights and a wreath drives through a festive night parade.
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Small Towns

The Remote Small Town in Maryland Locals Don’t Want You to Find

Tucked away between the Tussey and Warrior Mountains awaits Flintstone, Maryland, which is one of the most remote towns to visit.

by Beth Copenhaver
on Oct 26
chairs line the shoreline of the lake at rocky gap stte park in maryland in the fall
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Small Towns

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

Lusby, Maryland, offers a peaceful escape with natural wonders, maritime heritage, and charming attractions.

by Hugh Taylor
on Sep 14
A sandy beach with people walking along the shore, surrounded by trees and a cloudy sky.
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Small Towns

The Most Charming College Town In Maryland Is Home To Delicious Dining, Museums, And More

Salisbury, Maryland, offers a blend of history, delicious food, and unique attractions, making it a charming college town worth visiting.

by Hugh Taylor
on Sep 13
A serene lake reflects a modern building and colorful trees under a blue sky with wispy clouds.
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Small Towns

The Charming Small Town In Maryland That’s Perfect For A Fall Day Trip

Princess Anne in Maryland offers a perfect autumn day trip with its historic architecture and haunted locations.

by Hugh Taylor
on Sep 1
Historic red brick building surrounded by autumn foliage and a grassy area with fallen leaves.
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Small Towns

The Best Small Town Getaway In Maryland: Best Things To Do In Saint Michaels

Saint Michaels, Maryland, is a charming waterfront town known for its rich maritime history, scenic views, and friendly community, making it an ideal small town getaway.

by Megan Shute
on Jun 19
A serene harbor at sunset, with colorful skies reflecting on calm waters and boats docked along the shore.
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Small Towns

With a Farmers Market, Weekly Events, Live Music, and More, There’s Nothing Like a Sunday Morning in This Maryland Town

The Olney Farmers and Artists Market in Maryland offers fresh produce, live music, and unique vendors every Sunday, year-round.

by Hugh Taylor
on May 13
aerial shot of olney maryland on a sunny day
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Small Towns

Here Are The 10 Most Dangerous Towns In Maryland To Live In

Lists the ten most dangerous cities in Maryland based on violent crime rates.

by Jamie Alvarenga
on Jun 29
A city street lined with buildings under a bright blue sky with fluffy clouds, featuring a clock tower in the distance.
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Small Towns

You’ll Be Surprised To Learn That Arnold, Maryland Is One Of The State’s Best Coastal Towns

Arnold, Maryland offers unique coastal town experiences with riverside beaches, parks, and local dining.

by Hugh Taylor
on Jun 14
A calm waterfront scene with a dock, a boat, and wooden benches on a hazy day.
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Small Towns

You Could Spend Forever Exploring This Maryland Small City, But We’ll Settle For A Weekend

Ellicott City, MD offers a mix of historic sites, outdoor activities, and family-friendly attractions, making it a delightful place to explore.

by Megan Todaro
on Apr 20
A serene stream flows through a lush green area, flanked by historic buildings and trees in early spring.
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Small Towns

The Friendly Small Town in Maryland That’s Perfect for a Summer Day Trip

Havre de Grace, Maryland, is a charming coastal town perfect for a summer day trip with tons of shops, restaurants, and scenery just waiting to be explored.

by Megan Todaro
on May 6
The sun sets over the water near Havre de Grace, Maryland, with a pier in the distance
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Small Towns

Hike To A Cascading Waterfall, Then Dine At A Country Kitchen On This Delightful Adventure In Maryland

Explore Catoctin Mountain Park's Cunningham Falls Nature Trail and enjoy a meal at Thurmont Kountry Kitchen in Maryland.

by Megan Todaro
on May 15
A stone building with a sign reading "Visitor Center, Catoctin Mountain Park" surrounded by autumn foliage.
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Small Towns

This Maryland Town Is One Of The Most Peaceful Places To Live In The Country

Easton, Maryland is a charming small town known for its natural beauty, history, and vibrant arts scene.

by Megan Todaro
on Apr 12
Historic buildings line a sunny street, featuring brick facades and a pub, surrounded by lush green trees.
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Small Towns

Straddling The Maryland-West Virginia Border, The Town Of Hancock, Maryland Is One Of The Most Unique Places You’ll Ever Visit

Hancock, Maryland, is a unique small town with historical significance and scenic charm, located on the border of Maryland and West Virginia.

by Megan Todaro
on May 1
A street view featuring a mix of historic buildings, including a wooden inn and a brick structure, with parked cars.
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Small Towns

10 Small Towns In Maryland That Are Full Of Charm And Perfect For A Weekend Escape

Discover ten charming small towns in Maryland perfect for a weekend getaway, each offering unique attractions and local charm.

by Jamie Alvarenga
on Apr 21
Aerial view of a marina with boats, a lighthouse, and colorful buildings along the waterfront under a clear blue sky.
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Small Towns

The Surprising Maryland Town That Makes An Excellent Weekend Getaway

Boonsboro, Maryland offers charming parks, historic sites, and unique local businesses perfect for a memorable weekend stay.

by Jamie Alvarenga
on Jul 6
A street view featuring a sign for "Josie's on Main," American flags, and various buildings along a sunny road.
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Small Towns

Visit These 7 Quaint Beach Towns In Maryland Before The Tourists Arrive

Discover quieter beach towns in Maryland for a relaxing summer getaway.

by Jamie Alvarenga
on Mar 7
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Small Towns

You Can Live Off The Grid In This Maryland Town Considered To Be One The Best In The Country

Tilghman Island in Maryland offers scenic water views and a peaceful atmosphere, making it ideal for a getaway or off-the-grid living.

by Jamie Alvarenga
on Mar 7
A serene waterfront view at sunset, featuring a grassy area, flowers, a bench, and a distant pier.
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Small Towns

These 18 Charming Waterfront Towns In Maryland Are Perfect For A Daytrip

Explore the best waterfront towns in Maryland, each offering unique attractions and spectacular views.

by Jamie Alvarenga
on Mar 2
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Small Towns

15 Historic Towns In Maryland That Will Transport You To The Past

Explore the charm and history of Maryland's historic towns, each offering unique attractions and experiences.

by Jamie Alvarenga
on Mar 4
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Small Towns

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

Here are 12 small towns in Maryland to visit each month. Each is full of charm and makes for a lovely day trip.

by Jamie Alvarenga
on Jan 10
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Small Towns

The Unassuming Town Of Tilghman Island Is One Of America’s Best Hidden Gems For A Weekend Getaway

Tilghman Island in Maryland offers a memorable weekend getaway with waterside views, charming local businesses, and unique landmarks.

by Jamie Alvarenga
on Dec 13
A colorful yellow building with a green roof, featuring a shop front and an American flag, set against a clear blue sky.
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Small Towns

A Winter Getaway To Maryland’s Snowiest Town Is Nothing Short Of Magical

Oakland, Maryland, is a charming winter destination known for its snowy weather, holiday events, and natural beauty.

by Jamie Alvarenga
on Nov 17
A snowy landscape featuring a red brick building by a river, surrounded by trees and a wintery scene.
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Small Towns

This Maryland Christmas Town Is Straight Out Of A Norman Rockwell Painting

Berlin, Maryland is a charming Christmas town known for its festive events, horse-drawn carriage rides, and welcoming community.

by Jamie Alvarenga
on Nov 15
A horse-drawn carriage parked outside a building, featuring a sign for rides and colorful decorations.
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Small Towns

The Beach Town In Maryland That’s Surprisingly Perfect For A Holiday Getaway

Ocean City, Maryland, offers a festive holiday getaway with decorated hotels, themed dining, and light displays.

by Jamie Alvarenga
on Nov 11
A festive archway reading "Winterfest of Lights," adorned with colorful lights and candles, set against a night sky.
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Small Towns

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

Experience an old-fashioned Christmas in Pocomoke City, Maryland with carriage rides, caroling, and festive activities.

by Jamie Alvarenga
on Nov 8
A horse-drawn carriage decorated for the holidays, with children inside, passing by a building at night.
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Small Towns

The 10 Most Magical Christmas Towns in Maryland

Parades, Santa sightings, tree lightings, and more await in the Old Line State.

by Jamie Alvarenga
on Nov 4
main street in Hampden Baltimore, Maryland, decorated for Christmas