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Best Small Towns of Maryland!

Want to move to Maryland but everywhere you look it’s too big, too crowded or too busy?

In these days, many of us are still working from home and don’t need to worry about a long commute so living in one of these small towns is a possibility!

These MD Small Towns give you the best of Maryland without the stress of city/suburb living. Let’s go! 

Here are some of my top Small Towns in Maryland:

Berlin

Known for having a starring role in Runaway Bride with Julia Roberts, this small town has a thriving arts district and was ranked the “coolest small town in America” in 2014 by Budget travel! Berlin Main Street is a thriving and diverse community designated both as a Maryland Main Street Community and an Arts and Entertainment District located just 7 miles from Ocean City & Assateague Island. Like many other towns, Berlin hosts its share of movie nights, fireworks and concerts in the park – but then there are other events that are totally, uniquely, sometimes weirdly, Berlin.  

Check out some of their non traditional traditions – including their bathtub race where local businesses and competitors have been turning ordinary “tubs” into decked-out racing vehicles since 1992.

The 21 acres of Berlin, known as Stephen Decatur Park, are designated to provide playground and picnic facilities for families, as well as tennis and racquetball courts for the athletically-inclined. Dogs are also right at home in Berlin, where bowls of water sit outside of practically every store.

Population: 4,500. Median Home Value: $275,000

Hampstead

Taking a trip to Hampstead (just 30 miles northwest of Baltimore) is like traveling back in time.
Main St is reminiscent of quintessential small-town America, with gorgeous Colonial homes, an old-time police station, and antiques aplenty. 

Located in Carroll County, Hampstead was founded when Robert Owings started building a new road through the state. It was first called Spring Garden before changing its name to Hampstead. Originally settled by the English, the town was an agricultural hub due to its fertile lands.

History buffs can also marvel at several Civil War markers throughout town that eventually lead up to Gettysburg (an hour north). 

There’s also a huge water park, Cascade Lake, in town with water slides that drop you right into the spring-fed lake.

Population: 6,400. Median Home Value: $245,000

Thurmont

A small town in Frederick County, Thurmont is in the northern part of Maryland and quite close to the Pennsylvania border.

As it’s near two state parks, Thurmont has access to an abundance of natural beauty and is locally known as the “gateway to the mountains.” 

The awe-inspiring Cunningham Falls State Park is home to the largest cascading waterfall in Maryland

Additionally, the Catoctin Mountain Park features the edge of the Appalachian Mountains, hardwood forests and winding streams just a stone’s throw from Thurmont. 

The main town is quaint, with charming red-brick buildings and local independent shops aplenty.

Thurmont hosts Catoctin Color fest each year, an arts festival that attracts up to 125,000 people. 

While it may be small, Thurmont has a lot of surrounding attractions. This includes historic covered bridges that are perfect for taking a step back in time.

You can also get your hands on fresh fruit at Catoctin Mountain Orchard or go wine tasting at Springfield Manor Winery and Distillery.

Population: 6,200 Median Home value: $275,000

St. Michaels

St Michaels: The motto of St Michaels is “Historic Charm, Nautical Adventure, Romantic Spaces,” and this small town delivers on its promise.

A town in Talbot County, the town is named after the Episcopal Parish established there in 1677 well before the town was established in the 1700s.
St. Michaels was once a busy seaport and truly embraces small-town living.

Quaint, old-fashioned houses, boutiques and restaurants line the downtown area, while the harbor is a perfect spot to go for a stroll and relax while taking in the beautiful river views. 

The town is also home to the 19th-century Hooper Strait Light, one of only four Chesapeake Bay lighthouses built in the iconic screw-pile design; it remains one of St Michaels’ best attractions.

Today, people come from all over to enjoy a relaxing day by the water perusing unique shops along Talbot Street, sipping wine at the local winery and sailing on a harbor cruise through the bay.

Because St. Michaels is situated on the Chesapeake and was an important stop for sailors, its nautical history is quite impressive. 

It was also the grounds of a battle between the British and the Americans in the War of 1821, when it was targeted by the British because of a militia battery. According to local legend, the town was spared destruction from the cannonballs of the British by hanging lanterns out in the trees beyond the town, and thus becoming known as the town that “fooled the British”.

Make sure to stop by the Chesapeake Bay Maritime Museum when you visit to experience its 18-acre waterfront, outdoor and indoor exhibitions, marina and more.

Population: 1,100 Median Home Value: $417,000

Chesapeake City

On the Chesapeake & Delaware Canal, Chesapeake City is an idyllic little town filled with history and charm. 

It lies right on the edge of the waterfront and is bordered by trees and fields, which turn a lush green or a beautifully burnished bronze and orange according to the season, filling the town with color and warmth. 

Chesapeake itself is largely unspoiled, having retained an incredible proportion of its 19th-century buildings and houses, many of which have been converted into inns and restaurants. 

Meanwhile, the local museum is perfect for experiencing the town’s heritage and culture.

Population: 703 Median Home Value: $283,000

Crisfield

The waterside community of Crisfield in Somerset County, MD is the southernmost town in Maryland. Crisfield continues to be famous for its seafood throughout Maryland and the United States, particularly the Maryland Crab, and it abounds with restaurants, seafood packing houses, and seafood distribution companies. Several seafood restaurants across the country carry the city’s name. If you went any further south in Maryland you would wind up in the Chesapeake Bay, which is exactly how the town of Crisfield makes you feel.

Crisfield, a town in Somerset County, is located on the Tangier Sound on the Chesapeake Bay.

Referred to as “the crab capital of the world,” there’s plenty of boat fishing, marsh sanctuaries, maritime museums, and even a hard crab derby every Labor Day where the crustaceans race along in a shallow pool. Crisfield is a watermen’s town through and through.

Take in an unparalleled sunset at Wellington Beach, try a pint of Marsh Mud Oyster Stout at Chesapeake Brewing Co., or kayak through Janes Island State Park.

Population: 2,600 Median Home Value: $136,000

Easton

Easton is home to a stunning downtown area filled with upscale boutiques, incredible restaurants and eclectic art galleries.

Located halfway between Baltimore and Ocean City, this small town has kept its historic charm alive through beautifully restored buildings.

Easton has a bustling arts culture with outdoor summer performances, a busy concert schedule at The Avalon Theater, and a prestigious air painting competition at the annual Plein Air Art Festival. 

For those who love to spend time outdoors, Easton is along the Chesapeake Views bike loop, a 38.2-mile scenic trail offering some incredible water views. 

If you’re more into sailing, canoeing or kayaking, just hop in the automobile and you’ll be at the bay in just a few minutes.

Population: 16,600 Median Home Value: $386,000

Monkton

Monkton is a beautiful small town located 40 minutes north of Baltimore. 

A true country getaway, Monkton is A haven for those in need of a rural vacation, the area around this community is filled with sprawling countryside, horse farms, and historic old homes. 

Gunpowder Falls State Park surrounds this small town and the Monkton Station is a popular drop-off point for tubing down the river. 

While there are tons of trails throughout the park, one of the most unique is the Northern Central Railroad (NCR) Trail. The NCR trail goes through Monkton Station and runs along an abandoned railroad up to the Pennsylvania border.

No visit to Monkton is complete without stopping by Ladew Topiary Gardens. 

Here you’ll find 22-acres of award-winning gardens, a serene nature walk, the beautiful historic manor house and a quirky gift shop.

Stop by if you’re driving through, you’ll find it to be one of Maryland’s hidden gems.

Population: 4,860 Median Home Value: $668,000

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