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14 Towns Similar to Annapolis, MD

A view of Chesapeake bay in Annapolis, Maryland.

Annapolis, akin to the United States Naval Academy, is situated at Severn River’s mouth on the Chesapeake Bay, in Maryland in the United States. Annapolis is Maryland’s capital city and has an estimated population of 39,223 people ( the 2019 census). The living cost in Annapolis is 30% more than the national median.

With the exception of local and state governments, the leading employers in the city, as per the City’s 2018 Comprehensive Annual Financial Report, are the United States Naval Academy, with 2,500 employees, and the ARC of the Central Chesapeake Region, with 502 employees.

Annapolis has several tourist attractions and recreational facilities, including more than 200 acres of parks. It is a small, lovely town that boasts of colonial architecture. It hosts several holiday-themed or seasonal festivals and events across the year.

The museum receives over 100,000 guests annually. There is a vibrant community theatrical culture, with two locations in the old center. Colonial Players, located on East Street, presents roughly six performances each year in its 180-seat theater.

Then, during the summer, the Annapolis Summer Garden Theatre performs three plays on its outdoor stage, which may be seen from the City Dock.

1. Solomons Island, MD

This is an aerial view of Lexington Park in Solomon Islands, Maryland.

With an estimated population of 2,368 (2010 census), Solomons Island in Maryland, not to be confused with the Solomon Islands, is a well-known weekend resort in the Baltimore—Washington cosmopolitan region. Despite its modest size, it features three large hotels, a spiritual retirement home, and a family entertainment facility for the United States Navy.

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The town welcomes visitors with souvenir stores, seafood restaurants, a plethora of marinas, a sculpture park, a boardwalk, and the Calvert Marine Museum. Tourists may climb to the top of a historic lighthouse and listen to infrequent outdoor performances by notable musicians and board harbor cruises.

Solomons bears similarity with Annapolis in that they are both riverfront towns, have outdoor performances and Naval training bases. However, unlike Annapolis, Solomons is significantly smaller, with a population that’s almost 10% of Annapolis’s. The cost of living in Solomon’s is just under 20% higher than the national median.

2. Easton, PA

A view of Main Square in Easton, Pennsylvania.

Easton is positioned at Lehigh River and Delaware River’s confluence in Pennsylvania, USA. As of the 2019 census, the city’s population was estimated to be 27,189. A small town and a riverfront too, it bears much resemblance to Annapolis.

However, unlike Annapolis, there isn’t any Navy training base in Easton. Additionally, the cost of living is lower than the nation’s average at 83.8%. Natural resources abound in the surrounding region, including timber, slate, agriculture, and limestone.

With about 3,000 employees, Victaulic, who develops and produces mechanical pipe joining systems, is one of the largest employers in Easton. Following closely is Easton Hospital, with over 1,400 employees. Recreational activities include the Crayola Experience, an attraction site for crayon-centric activities, the Crayola Factory, and National Canal Museum.

Hotel accommodation ranges around $133 though you can get budget-friendly options from $87.

3. Chestertown, MD

This is a view of the sidewalk in the business district of Chestertown.

Another small river town, with historic colonial architecture, drawing similarity to Annapolis, is Chestertown. Similarly, it hosts several annual events and festivals. Chestertown is situated along Chester River’s banks in Maryland, USA.

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However, the population is incomparable to that of Annapolis. The 2010 census indicates an estimated population of 5,252.

Its historic sites, brick walkways, wide culinary variety, winery, and charming antique shops entice inhabitants and visitors to browse, explore and gaze. The town’s largest industries are Educational Services, with just over 500 employees, and Retail Trade, with slightly over 400 employees. You’ll get hotel accommodation at an average of about $80.

The overall cost of living is slightly below the nation’s average.

4. Fredericksburg, VA

This is an aerial view of the historic town of Fredericksburg.

President George Washington’s childhood home location, Fredericksburg, is a city located in Virginia, USA. Its population is similar to that of Annapolis, standing at an estimated 29,036 as of 2019. Its most significant employers are the University of Mary Washington and Mary Washington Healthcare, both named after George Washington’s mother.

Much of the town’s tourism economy is tied to this heritage, including sites associated with George Washington and historic Georgian houses. This makes it very different from Annapolis. The area has restaurants, parks, and coffee shops. The average living cost is 7% more expensive than the national median. $50 will get you budget hotel accommodation.

5. Havre de Grace, MD

This is a view of the seaside are in Havre de Grace city.

Like Annapolis, Havre de Grace is a small city positioned at the Susquehanna River’s mouth. Its location is in Harford County in Maryland, US. As of 2019, the estimated population was 14,018.

A beautiful, scenic area, Travel World ranked it among America’s top 50 small towns, and Smithsonian Magazine named it one of the best to visit among America’s small towns.

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Unlike Annapolis, whose top employer is the Navy, in Havre de Grace, leading employers are The John Hopkins University and Southwest Airlines, totally different industries. Also, it is among the more expensive cities with a living cost 28% higher than the nation’s median. On average, you can get decent accommodation for $55 traveling on a budget.

Top attraction sights include Mount Felix Winery and Vineyard, Susquehanna State Park, and Concord Point Lighthouse.

6. Cambridge, UK

This is an aerial view of the historic Cambridge in UK.

Cambridge is Cambridgeshire’s County town and a university city in the East of England. Located on the River Cam, it is similar to Annapolis in this aspect. While Cambridge is regarded as one of the UK’s most expensive cities to live in, owing primarily to housing expenses, it is 25.41% less costly than New York (excluding rent).

Like Annapolis, there are several attraction sites within walking distance from the town’s center. Attraction sites include a modern and antique museum, heritage botanical garden, and contemporary art gallery.

Its main difference with Annapolis is that Cambridge has double the area coverage, and the population, at 124,798 in 2019, is a quarter the people of Annapolis. Manufacturing is the area’s primary sector, employing around one-fifth of the workforce. On average, decent hotel accommodation will cost about $54.

7. Saint Michaels, MD

St. Michaels, located in Talbot County in Maryland, is a miniature town compared to Annapolis. Its total surface area is a ⅐ of Annapolis. In 2019, St. Michaels estimated population was 1,040. Though not a tourist attraction until the 1970s, a maritime museum, tour boat, and seafood restaurant on the waterfront draw visitors to this tiny town.

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Like Annapolis, it is a waterfront town, with the museum as a significant point of interest. Its primary industries are seafood and shipbuilding. The living cost is 25% above the national average.

Hotel accommodation will cost an average of $100. This delightful town is loaded with excellent restaurants, one-of-a-kind stores, and lively marinas, and stunning houses and landscapes that are all well-tended.

8. Oxford, UK

This is an aerial view of the historic Oxford in UK.

Oxford, dubbed the “City of Spires” due to its fantastic skyline of Gothic steeples and towers, is located on the outskirts of one of England’s distinctive and picturesque areas. Additionally, it boasts magnificent green spaces. Famous for Oxford University, purportedly the second oldest globally, it is frequently rated as the most outstanding university globally, having produced 28 Nobel laureates. This makes it very different from Annapolis.

The Thames and Cherwell Rivers stream through the city, coming together on the city’s south side, drawing the town’s similarity to Annapolis. However, it occupies double the surface area and has 3.9 times the population (152,450 as of 2017). Its main industries are education, biotechnology and health, and publishing.

9. Lancaster, PA

This is an aerial view of Lancaster City in Pennsylvania.

One of the most populated Amish communities in America, unlike Annapolis, Lancaster is a South-Central Pennsylvania city in the US. Its population was 59,433 in 2019. The overall living cost is 86.8% – lower than the national average.

The town bears many similarities to Annapolis in its offering of distinctive architecture, enthralling live performances, unique art exhibitions, vibrant theatre, and historic sites. It is a walkable town.

Lancaster also offers one-of-a-kind boutiques and excellent eating options. Its major industries are healthcare, manufacturing, tourism, and public administration, with Armstrong World Industries and Penn Medicine Lancaster General Health among its top employers. The living cost in this town is below the national average at 86.8%. $60 will get you decent hotel accommodation.

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10. Crisfield, MD

This is a close look at the Harbor in Crisfield, Maryland.

Crisfield is positioned on Chesapeake Bay’s Eastern Shore, on the Tangier Sound, in Somerset County in Maryland, USA. It is well-known for its wildlife, simple way of life, natural beauty, hard work, a strong sense of unity, Watermen, and most importantly, its seafood – particularly the Maryland blue crab. It’s no wonder its nickname is The Seafood Capital of the World.

It’s a tiny town with a population of 2,515 based on the 2020 census. Unlike Annapolis, Social Assistance and Health Care are its largest industry with 167 employees. For tourist activity, the town has lots of biking and water opportunities. Additionally, the living cost is lower than the national average, at 77.5%.

The only similarity with Annapolis is that it is a small town and has a waterfront. Today, the city is a significant tourist attraction on the Chesapeake Bay, holding yearly special events like the National Hard Crab Derby. The average budget accommodation ranges around $50.

11. Leonardtown, MD

Leonardtown is a minor, lovely neighborhood in which to raise a family. As a great rural region with many possibilities for families, there are several outdoor activities to choose from but don’t anticipate clubs.

Like Annapolis and hosting annual events, the national oyster-shucking championship, held annually at the St. Mary’s County fairgrounds, is probably Leonardtown’s most prominent feature. The town is positioned close to the Patuxent River Naval Air Station.

Leonardtown has a population of only 3,824 as of 2019. In comparison, almost a tenth of Annapolis’s people, the total square footage of Leonardtown is 10.04 km2 – half the size of Annapolis. Some of the top attractions are historical sites, a winery, and a harbor. Public Administration forms an extensive industry with over 370 employees.

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The living cost is above the national average by 20.3%, and budget-friendly hotel accommodation ranges from $75.

12. North East, CHSPK

North East is a hamlet on the Chesapeake Bay’s crest that is home to boutiques and fishers. You may spend a great day shopping or participate in outdoor activities. Like Annapolis, this is a riverfront town, has close-by attractions you can walk to, and has several historic homes.

You can enjoy the scenery, feed the ducks, and even fish at the fantastic park located on the Susquehanna River. Its population is about 2,000.

The North East River begins north of here, runs through town, and expands towards the southern end. One side of the town’s main street has a beautiful river bordering it, similar to Annapolis. Situated at Walnut Street’s end, The Upper Bay Museum houses one of the area’s extensive fishing and hunting artifacts collections.

Visitors may stroll down Main Street and find handcrafted items and antiques, and many eateries. An average of $85 will get you decent hotel accommodation. The average cost of living is 7.3% above the national median.

13. St. Mary’s City, MD

St. Mary’s City is a really tiny town that has St. Mary’s River bordering it, drawing similarity to Annapolis. It was a colonial town and is situated in Maryland. Its population in 2010 was at 933. Where Annapolis is to Navy, St. Mary’s is to archeology.

It is the location of the Historical Archaeology Field School and an internationally known archaeological study area and archaeologist training site.

St. Mary’s College of Maryland and Patuxent River Naval Air Station are both located in the county. St. Mary’s County has consistently been recognized for its distinct and historical culture of crabbing villages, Chesapeake Bay tidewater fishing, and farming. This miniature town is often regarded as the origin of religious liberty in the United States.

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Its largest employers are the Grand Lake Health System and Setex (an automotive seat manufacturer). The cost of living I significantly higher than the national median at 55.6%.

14. Rock Hall, MD

Rock Hall is more than just a retail center. It is an amazing boating community with over a dozen marinas. It is located in Maryland, US.

This bayside town provides a range of maritime activities, a public beach, and miles of shoreline to explore. This Kent County hamlet is known as the “Pearl of the Chesapeake.” Like Annapolis, this town has a significant presence of an artistic community and offers events, shows, races, contests, and festivals.

The population, as of 2019, is at 1,340, out of whom only 491 have gainful employment. The primary industry in this town is seafood processing. Recreational activities include birdwatching, hiking, hunting, fishing, sunning, boating, or just relaxing as you sip your favorite beverage.

The living cost is slightly below the national median at 93.0. Hotel accommodation will average about $100.