11 Charming Small Towns in Maryland You Need to Visit in 2026

Small towns in Maryland hide fascinating stories, such as how Havre de Grace lost becoming the nation’s capital by only 1 vote. The town dates back to 1695, and this historic waterfront destination represents just one of many charming places scattered throughout the state.

The best small towns in Maryland provide a variety of experiences. Travelers can explore small towns near Baltimore like Ellicott City or find small beach towns in Maryland such as Chesapeake Beach. This piece covers 11 cute small towns in Maryland worth adding to your 2026 travel list, from historic ports to mountain retreats.

Havre de Grace

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Why Visit Havre de Grace

Havre de Grace sits at the mouth of the Susquehanna River where it meets the Chesapeake Bay, approximately 35 miles north of Baltimore in Harford County. The Marquis de Lafayette gave the town its name during the American Revolution, reminded of the French port city Le Havre. This waterfront destination houses around 13,000 residents. It serves as one of Maryland’s second oldest municipalities, incorporated in 1785.

The town’s walkable historic district spans less than 2 miles from north to south, with ample parking throughout. Visitors arriving by car can access the area from Interstate 95. Boaters can reach the marinas by following the dredged channel markers. The mile-long Havre de Grace Promenade provides waterside access along the Susquehanna River.

Top Attractions in Havre de Grace

The Havre de Grace Promenade ranks as the top attraction with a 4.6 rating. Susquehanna State Park follows at 4.5. The park sits 10 minutes from downtown and features camping, hiking trails and remnants of the Susquehanna and Tidewater Canal.

Concord Point Light dates to 1825 and stands as the oldest publicly available lighthouse on the Chesapeake Bay. The adjoining Keeper’s House Museum displays educational exhibits about this landmark at the corner of Concord and Lafayette Streets.

The Havre de Grace Decoy Museum earned a 4.7 rating. It houses one of the finest collections of working and decorative Chesapeake Bay decoys. The town holds the title “Decoy Capital of the World”. The Havre de Grace Maritime Museum preserves the area’s rich maritime heritage with more than 20 permanent exhibits, an environmental center and a boat shop that restores wooden boats.

Millard Tydings Memorial Park covers eight acres with picnic areas, a playground and a pavilion overlooking the Susquehanna River. The Susquehanna Museum at the Lock House occupies the original 1840 lock tender’s house and preserves canal history with an original lock and working swing bridge.

Where to Eat in Havre de Grace

Water Street Seafood, 80 years old, serves local and regional favorites including steamed crabs and oysters with waterfront views. The restaurant offers wine and beer from surrounding wineries and breweries, plus craft cocktails. It holds a 4.5 rating.

Tidewater Grille provides fresh seafood with waterfront dock access and carries a 3.7 rating with 771 reviews. The Vineyard Wine Bar scores 4.4 with 317 reviews. MacGregor’s Restaurant, 37 years old, has served upscale-casual American and fish-focused fare for over 35 years on the Susquehanna River waterfront.

Where to Stay in Havre de Grace

The Vandiver Inn features concierge services, non-smoking rooms, a garden and free Wi-Fi, with rates starting from $160.55 per night and a 9.2 guest rating. Super 8 by Wyndham Havre de Grace Aberdeen Area sits 5 minutes from downtown and serves daily breakfast with rates from $55.89 and a 6.5 rating.

Spencer-Silver Mansion and the Old Chesapeake Hotel provide additional lodging options. Nearby Aberdeen offers several chain hotels, including Holiday Inn Express Aberdeen-Chesapeake House with rates from $106.00.

St. Michaels

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Why Visit St. Michaels

Founded in 1672, St. Michaels grew from a shipbuilding community that produced Native American-inspired dugouts and swift Baltimore Clipper schooners. British forces targeted the yards in 1813, but residents used lanterns to misdirect enemy gunfire and earned the designation “the town that fooled the British”. This maritime progress birthed the bugeye, a schooner-rigged vessel that became essential to local watermen.

The Inn at Perry Cabin gained recognition as the filming location for the wedding reception scene in the 2005 film Wedding Crashers. St. Michaels sits on Maryland’s Eastern Shore, 1.5 hours from Washington, D.C., and houses about 1,000 full-time residents. The harbor serves as the town’s focal point and provides views into maritime heritage.

Top Attractions in St. Michaels

The Chesapeake Bay Maritime Museum ranks as the top attraction with a 4.6 rating. This 18-acre interactive facility features Chesapeake Bay artifacts and exhibitions alongside a floating fleet of historic boats. The 1879 Hooper Strait Lighthouse allows visitors to climb for harbor views. The museum’s 1920 Winnie Estelle boat provides scenic river cruises.

Talbot Street, the main strip, displays restored colonial buildings and unique shops with restaurants. Lyon Rum distillery offers free samples seven days a week. The Oxford-Bellevue ferry, one of the country’s oldest privately held ferries, connects to Oxford.

Where to Eat in St. Michaels

Ruse, led by chef Michael Correll, received a 2025 James Beard nomination for Best Chef: Mid-Atlantic. The restaurant scores 4.8 with 24 reviews and serves reimagined Eastern Shore dining. The Crab Claw, a 50-year-old institution, operates seasonally from April through November and serves fresh Chesapeake seafood.

Ava’s Pizzeria scores 4.5 with 1,454 reviews and offers wood-fired pizza in a family-friendly setting. Limoncello Italian Restaurant earns 4.4 with 573 reviews for homemade pasta. Bistro St. Michaels provides French-influenced cuisine with a 4.5 rating.

Where to Stay in St. Michaels

The Inn at Perry Cabin features a spa, yoga, croquet, and tennis courts with waterfront seating and free bicycles. The property dates to the early 1800s with modern rooms and maritime-inspired design. Stars Restaurant operates on-site.

The Wildset Hotel occupies four 19th-century buildings updated with minimalist decor. The 34-room property provides free breakfast and bicycles with s’mores kits, and rooms have private balconies, gas fireplaces, and soaking tubs. St. Michaels Harbor Inn, Marina & Spa sits on the historic harbor with marina access.

Places to visit in Maryland.

Chesapeake Beach

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Why Visit Chesapeake Beach

Once known as the “Playground of the Potomac,” Chesapeake Beach drew attention from over 10,000 weekend visitors during the early 1900s. The Chesapeake Beach Railway Company founded this waterfront community in the 1890s as a resort destination. This legacy continues to shape the town’s identity more than 130 years later. The town sits 35 miles southeast of Washington, D.C. along the western shore of the Chesapeake Bay in Calvert County. This family-focused community blends small-town character with coastal experiences.

Day trips or weekend getaways from Baltimore and Annapolis remain available. Visitors can explore the scenic Chesapeake Beach Railway Trail or visit the Chesapeake Beach Railway Museum to view artifacts and photographs from the resort era. The neighboring town of North Beach sits minutes away, connected by shared shoreline and regional events.

Top Attractions in Chesapeake Beach

The Chesapeake Beach Railway Museum occupies the original 1898 railway station. The museum chronicles how the railroad transformed this remote area into a thriving resort. An original passenger car, photographs, and artifacts from the railway era fill the museum. It operates from May through September with free admission.

Chesapeake Beach Water Park features eight water slides, fountains, waterfalls, and a lagoon with bay views. The facility operates from Memorial Day weekend through Labor Day and offers cabana rentals for shade and private relaxation. The town’s boardwalk stretches along the waterfront and connects to a 700-foot fishing pier where anglers catch spot, croaker, and striped bass.

Breezy Point Beach earned a 3.5 rating and provides fossil hunting opportunities. Prehistoric shark teeth from the Calvert Cliffs formation dating back 15-20 million years can be found here. The Chesapeake Beach Railway Trail scored 4.4 with 44 reviews.

Where to Eat in Chesapeake Beach

Rod ‘N’ Reel Restaurant, 78 years old, serves as the heart of the resort with caught seafood and locally inspired dishes. The renovated restaurant features waterfront views and operates Wednesday through Sunday, with breakfast available on weekends. The venue holds a 3.5 rating with 419 reviews.

Baia Coastal Italian Kitchen & Wine Bar sits on the water and offers coastal Italian cuisine, house-made pastas, and a large Italian wine program. The restaurant scored 4.5 with 12 reviews. Traders Seafood Steak and Ale earned 3.7 with 199 reviews.

Where to Stay in Chesapeake Beach

Rod ‘N’ Reel Resort provides waterfront accommodations with two on-site marinas, a rooftop pool, indoor pool, fitness center, and complimentary Wi-Fi. The resort scored 3.8 with 776 reviews. Guests access gaming facilities, live entertainment, and multiple dining venues including CBQ for breakfast and 1936 Bar & Grill. The Brant Nantucket earned 4.9 with 21 reviews, while The Inn at Herrington Harbor scored 4.5 with 188 reviews.

Ellicott City

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Why Visit Ellicott City

Three Quaker brothers founded Ellicott City in 1772 and established what would become one of the most prominent milling and manufacturing towns in the east by the 1860s. This picturesque mill town sits between Baltimore and Washington, D.C., under 30 minutes from Baltimore. That makes it an available escape among small towns near baltimore.

Historic Main Street features classic 18th and 19th-century architecture paired with modern boutiques and cafes. The town played a vital role as a stop on the Baltimore and Ohio Railroad, the first major railroad in the country. More than 70 eclectic boutiques, shops, art galleries and dining options now occupy these historic streets.

The OEC Trolley provides free rides through Historic Ellicott City from 11 AM to 7 PM on weekends and arrives every 10 to 15 minutes. Visitors can park once and ride with ease to explore Main Street’s unique offerings.

Top Attractions in Ellicott City

The B&O Ellicott City Station Museum preserves the railroad heritage that shaped this community. Families can explore exhibits before wandering the picturesque streets to get ice cream or baked goods.

Ellicott City Distilling Co. offers locally crafted spirits, while Artist’s Gallery showcases the region’s artistry. Solo travelers find peaceful spots at Backwater Books to journal. Clayground provides pottery workshops to get hands-on creative experiences.

Festivals, eclectic shops and vibrant street art tell the town’s creative story throughout the year. The walk from beginning to end of Main Street takes about 45 minutes.

Where to Eat in Ellicott City

Manor Hill Tavern occupies the historic Taylor’s Row, where exposed stone walls, barn doors and vaulted ceilings complement creative dishes paired with fresh brews from their family-owned farm. The venue serves as a perfect blend of old and new.

Maryland’s Koreatown features a self-guided tour revealing beloved restaurants and late-night lounges to enjoy Korean BBQ, soju cocktails and karaoke. Roggenart serves flaky croissants and espresso, while EC Diner offers classic milkshakes. Alexandra’s at Turf Valley Resort provides patio dining with scenic views and seasonal menus. Georgia Grace Café and Tersiguel’s French Country Restaurant deliver farm-to-table establishments in 19th-century settings.

Where to Stay in Ellicott City

Turf Valley Resort provides staycation packages with resort amenities. Residence Inn by Marriott Columbia offers extended-stay accommodations. The Wayside Inn and Inn At Mary’s Land Farm round out lodging options in this charming destination.

Maryland puns.

Frederick

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Why Visit Frederick

Western Maryland’s Frederick blends Civil War heritage with a flourishing culinary scene that attracts food enthusiasts from the East Coast. The town sits less than two hours from Washington, D.C.. The historic downtown district alone houses over 30 restaurants. Frederick was founded in 1748 and has a current population of 70,000. History buffs and culinary travelers rank it among the best small towns in Maryland.

Carroll Creek Linear Park stretches 1.5 miles through the historic district. Pedestrian paths, public art and bridges create an urban oasis atmosphere. The brewing district along this waterfront corridor has earned Frederick recognition as one of the brewery capitals of the mid-Atlantic, with 41 craft beverage purveyors throughout the county.

Top Attractions in Frederick

The National Museum of Civil War Medicine holds a 4.5 rating. It chronicles medical breakthroughs from the Civil War era. Historic Downtown Frederick earned 4.7, where 18th and 19th-century architecture houses boutiques, art galleries and specialty shops. The Weinberg Center for the Arts occupies a restored 1920s movie palace. Frederick Keys Baseball provides minor league entertainment at Harry Grove Stadium.

Monocacy National Battlefield preserves the site known as “The Battle That Saved Washington”. Visitors can explore covered bridges throughout the countryside and sample wines along the Frederick Wine Trail.

Where to Eat in Frederick

Bryan and Michael Voltaggio, natives who appeared on Top Chef, opened Wye Oak Tavern near their boyhood home. The Wine Kitchen on the Creek scores 4.4 and pairs creative cuisine with extensive wine selections along Carroll Creek. Fifty Fifty developed a cult following for burgers made with half beef, half bacon patties.

Hootch and Banter serves modern American fare. Thai Meric Eatery & Bar features traditional recipes from Chef Pimpisa Huynh’s grandmother. Hinzi’s Kitchen offers Pakistani specialties, and Dutch’s Daughter has served the community since 1984.

Where to Stay in Frederick

Frederick County provides bed-and-breakfasts with preserved architecture and modern hotels from boutique properties to national brands. Vacation rentals are available in both downtown and countryside settings. Many accommodations offer pet-friendly options. Gambrill State Park provides camping with amenities.

Berlin

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Why Visit Berlin

Recognized as “America’s Coolest Small Town,” Berlin sits just minutes inland from Ocean City. The town provides Victorian charm without beach crowds. Publications including Oprah and Esquire gave this Eastern Shore destination its nickname. The town preserves 47 individual structures on the National Register of Historic Places. These structures represent nearly two centuries of architectural heritage that spans Federal, Victorian, and 20th Century periods.

Berlin’s tree-lined streets and brick storefronts maintain uniform setbacks and compatible rooflines. This creates a cohesive historic district. The town participated in filming Runaway Bride and serves as part of the StoryWays: A Trip of Faith & Freedom self-guided mural and history tour. The tour shares African American history from Maryland’s Eastern Shore.

Assateague Island National Seashore lies 15 minutes away. Wild ponies graze along the dunes there. Visitors can explore nature trails, rent kayaks through Ayers Creek Adventures, or visit Herring Creek Nature Park to watch birds.

Top Attractions in Berlin

Historic Main Street anchors the downtown experience. Independent shops include Beach Memories Glassworks, The Greyhound Indie Bookstore, and World of Toys. The Mermaid Museum opened in March 2025 and displays interactive artifacts and folklore that celebrate mythical sea creatures. The Globe, a renovated 1917 theater hall, hosts live concerts with regional and national acts.

Where to Eat in Berlin

The Sterling Tavern operates seven days weekly from 11 AM to 11 PM. The menu includes house-made jumbo lump crab cakes, fried avocado with crab salad, and scallop cheesesteak with 12 beers on tap. Chef Justine Zegna owns Blacksmith Bar & Restaurant and emphasizes farm-to-table dishes with local ingredients. The restaurant maintains a walk-in only policy. Burley Oak Brewing Company, 14 years old, gained recognition for craft beers like Sorry Chicky sour.

Where to Stay in Berlin

The Atlantic Hotel, built in 1895, features Victorian-period style. Rooms include four-poster beds, vintage wallpaper, and marble-top dressing tables. The Inn Berlin Bed and Breakfast occupies a Victorian estate over two centuries old. Five guest rooms come with private baths, organic linens, Smart TVs, and complimentary gourmet breakfast.

Providenciales.

Chestertown

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Why Visit Chestertown

Brick-lined streets showcase well-kept 18th-century homes in Chestertown, where Simon Wilmer donated land in 1706 to establish this Eastern Shore port town. Washington College, chartered in 1782 as the first college in the United States, anchors the Arts & Entertainment District. The Chester River flows along Water Street, where Georgian and Federal-style architecture has Widehall (1770) and the Watkins-Bryant House (1730), thought to be the oldest residence on the waterfront. This historic downtown, listed on the National Register of Historic Places, houses over 200 specialty shops and restaurants.

Top Attractions in Chestertown

MassoniArt Gallery earned 4.6 as the top attraction, while the Historical Society of Kent County scored 4.5. The Garfield Center for the Arts at the Prince Theater occupies a restored 1920s venue. Annual events have the weekly Farmers’ Market and Dickens of a Christmas festival in December. The White Swan Tavern, built in 1733 and converted to a tavern in 1790, hosted George Washington during visits to Chestertown. A self-guided historic walking tour features 25 stops through the downtown district.

Where to Eat in Chestertown

Watershed Alley received 4.6 and specializes in refined regional cuisine. The Kitchen at the Imperial scored 4.1 with 242 reviews and serves elevated meals in a warm atmosphere. Modern Stone Age Kitchen, founded by food anthropologist Dr. Bill Schindler, focuses on fermented foods and traditional preparation methods without industrial fats or refined sugar. Luisa’s Cucina Italiana earned 4.5 with 315 reviews and prepares authentic Italian dishes with fresh ingredients.

Where to Stay in Chestertown

Brampton 1860 earned 4.9 with 898 reviews and features seven rooms in the 1860 manor house plus six cottages on 35 acres. Great Oak Manor scored 4.8 with 745 reviews and offers 12 rooms on 15.2 acres with Chesapeake Bay views and a private beach.

North Beach

Why Visit North Beach

Often called the “Jewel of the Chesapeake Bay”, North Beach sits on the western shore with a population of 2,014. This waterfront destination features a seven-block waterfront anchored by a half-mile-long boardwalk that extends to the bay at the southern end and opens to sandy beaches at the north end. Park benches line the pathway to watch boats sail across the water.

The town lies close to Washington, D.C., Baltimore, and Annapolis. You can reach it via Interstate 95/495 to Route 4 south, then Route 260. The drive from the capital takes 40-45 minutes. Annual events include the House & Garden Tour and Bayfest, while weekly activities feature farmers markets and live music on the boardwalk.

Top Attractions in North Beach

The North Beach Boardwalk provides stunning Chesapeake Bay views with informational plaques about local wildlife and designated fishing areas. Bayside History Museum offers exhibits on the town’s development as a summer resort destination. The sandy beach accommodates swimming and sunbathing with lifeguards on duty during peak season.

Where to Eat in North Beach

Ketch22 scored 4.0 with 84 reviews, while Hook & Vine Kitchen and Bar earned 3.9 with 111 reviews. Neptune’s Seafood Pub, operating for almost four decades, serves fresh seafood in a casual setting and holds a 3.8 rating with 188 reviews. Plaza Mexico Restaurant scored 4.0.

Where to Stay in North Beach

Anchored Inn At Hidden Harbor Marina features rates starting from $149.00 and earned a 9.2 guest rating. Rod ‘n’ Reel Resort scored 8.6 with 1,070 reviews and rates from $141.00. The Inn at Herrington Harbor earned 4.5 with 188 reviews.

Salvador Brazil.

Boonsboro

Why Visit Boonsboro

Brothers George and William Boone, cousins of frontiersman Daniel Boone, founded Boonsboro in 1792 by laying out 44 half-acre lots along a wagon road. This walkable town sits at the foot of South Mountain and has approximately 3,500 residents. Brick sidewalks line the streets. Shops filled with local art dot the downtown. New York Times bestselling author Nora Roberts operates Turn the Page Bookstore with her husband Bruce Wilder. Lines of fans wrap around the corner during book signings.

Top Attractions in Boonsboro

Citizens built the first monument dedicated to George Washington in 1827 atop South Mountain. It rises 34 feet. The Boonsborough Museum of History houses Civil War collections from Antietam and Gettysburg campaigns. It opens May through September. Crystal Grottoes Caverns sits less than 10 minutes from Antietam Battlefield. The National Road Museum and Trolley Museum preserve transportation history along the Historic National Road.

Where to Eat in Boonsboro

Jeovani’s Pizzeria serves traditional Italian meals with a full bar. The Admiral, owned by the team behind Captain Bender’s Tavern, offers upscale dining that includes crab soup and lobster mac and cheese. Branded Chophouse specializes in top-grade steaks and seafood. Sunday brunch features bottomless mimosas.

Where to Stay in Boonsboro

Inn Boonsboro combines boutique hotel luxury with bed-and-breakfast warmth in the heart of historic downtown and offers getaway packages.

Oakland

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Why Visit Oakland

Western Maryland mountains frame Oakland and offer a completely different point of view of the state beyond the Chesapeake Bay regions. This county seat received Main Street Maryland designation from the 26-year-old program. The town attracts visitors seeking proximity to Deep Creek Lake and Swallow Falls State Park, with clean mountain air and average summer temperatures of 75 degrees. The Autumn Glory festival draws more than 50,000 people over a week.

Top Attractions in Oakland

Downtown hosts three museums. The Oakland B&O Museum occupies an 1884 Queen Anne Style train station. The Garrett County Museum of Transportation displays old cars, buggies, sleighs and exhibits about Deep Creek Lake history. Broadford Recreation Area provides volleyball and basketball courts, swimming areas, five pavilions for rent, grills, picnic areas, playgrounds and a boat launch. Swallow Falls State Park features Muddy Falls.

Where to Eat in Oakland

Englander’s opened as a pharmacy with a soda fountain in the 1940s. The antique store operates the original soda fountain for meals. Dutch’s at Silver Tree earned a 4.4 rating with 486 reviews. Ace’s Run Restaurant & Pub scored 4.2 with 368 reviews, and Brenda’s Pizzeria received 4.5 with 532 reviews.

Where to Stay in Oakland

The Garrett Inn, Oak-Mar Motel, Haley Farm Inn and Retreat Center, and Inn At Deep Creek provide lodging options.

Weekend getaways from Baltimore.

Easton

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Why Visit Easton

The 8th Best Small Town in America, Easton houses over 16,500 residents in a sophisticated center founded in 1790. This destination stands out among small towns to visit in maryland for culinary excellence and sits one hour from Baltimore, Annapolis, and Washington. Paul Prager’s Bluepoint Hospitality Group transformed downtown with over a dozen curated restaurants and shops that locals call “Pragerville”. The town offers theatrical performances, music venues, and galleries along tree-lined streets with Colonial and Victorian architecture.

Top Attractions in Easton

The annual Waterfowl Festival draws 18,000 visitors each November and features 450 artists who exhibit wildlife paintings and carvings at 18 sites. Carroll Creek Linear Park and the Plein Air Competition attract art enthusiasts. The Chesapeake Chamber Music Festival presents world-class performances in June. Historic downtown walking tours showcase specialty shops and antique stores.

Where to Eat in Easton

Out of the Fire earned 4.6, while Bas Rouge scored 4.7 for fine-dining European cuisine. Legal Assets received 4.5, and Scossa Restaurant got 4.5 for Italian fare. Bluepoint establishments include Sunflowers & Greens for salads and The Wardroom’s gnocchi bar.

Where to Stay in Easton

Tidewater Inn anchors downtown accommodations, while Fairfield by Marriott and Best Western Plus provide modern options. Bishop’s House Bed and Breakfast offers Victorian charm.

Comparison Table

Enjoy Small Towns in Maryland

Maryland’s small towns offer a variety of experiences, from waterfront escapes like St. Michaels and Havre de Grace to mountain retreats such as Oakland. Each destination presents its own character. Visitors can seek Civil War history in Frederick or Victorian charm in Berlin. The beauty of these 11 towns lies in their accessibility, with most positioned within easy reach of major cities yet feeling worlds apart. Travelers planning their 2026 itinerary should pick several towns to explore based on personal interests. These communities prove that memorable getaways don’t require extensive travel, just the willingness to find hidden gems.

FAQs

Q1. Which Maryland small town is considered the best to visit? Several Maryland small towns stand out for different reasons. St. Michaels is renowned for its maritime heritage and upscale dining, while Berlin has been recognized as “America’s Coolest Small Town.” Easton ranks as the 8th Best Small Town in America and offers sophisticated culinary experiences. The best choice depends on your interests—whether you prefer waterfront settings, historic architecture, or mountain scenery.

Q2. What makes Maryland’s Eastern Shore towns so attractive to visitors? Eastern Shore towns like St. Michaels, Chestertown, and Berlin offer a unique combination of Chesapeake Bay waterfront views, well-preserved colonial and Victorian architecture, and rich maritime history. These communities feature walkable historic districts filled with boutique shops, art galleries, and seafood restaurants. Many also provide access to water activities like boating, fishing, and kayaking while maintaining a relaxed, small-town atmosphere.

Q3. What is Maryland’s top tourist attraction? Maryland offers diverse attractions across its small towns. The Chesapeake Bay Maritime Museum in St. Michaels is highly rated for its interactive exhibits and historic lighthouse. The National Museum of Civil War Medicine in Frederick provides unique historical insights. For natural beauty, Swallow Falls State Park near Oakland and Assateague Island near Berlin attract many visitors with their scenic landscapes and wildlife.

Q4. Which charming town should I visit along Maryland’s Historic National Road? Boonsboro is an excellent choice along the Historic National Road. This walkable town features brick sidewalks, local art shops, and the first monument dedicated to George Washington, built in 1827. The town also houses the National Road Museum and offers proximity to Civil War sites like Antietam Battlefield, making it perfect for history enthusiasts.

Q5. How far are Maryland’s small towns from major cities? Most of Maryland’s charming small towns are conveniently located within 1-2 hours of major cities. Havre de Grace sits 35 miles north of Baltimore, while Chesapeake Beach is 35 miles southeast of Washington, D.C. Ellicott City is under 30 minutes from Baltimore, and Frederick is less than two hours from the capital. This accessibility makes them ideal for day trips or weekend getaways.