11 Picturesque Towns in Maryland for a Weekend Retreat in 2024
When it comes to exploring The Old Line State, which was chartered as a colony in 1632 and ultimately ratified the US Constitution in 1788, large cities like Baltimore often dominate the conversation. However, beyond the urban bustle lies a plethora of charming small towns, each offering a rich history, beautiful architecture, and distinctive local culture. From the Victorian allure of Berlin to the maritime roots of St. Michaels, these treasures make for a tranquil weekend escape and provide a window into Maryland’s celebrated past. This year, trade the congested streets for cobblestone lanes and discover the quaint, historic towns described below.
St. Michaels
St. Michaels, the oldest town in Talbot County, dates to the mid-1600s, when it served as a trading post for area trappers and tobacco farmers. Its earliest industry was shipbuilding, with the town’s shipyards and the presence of a military battery making it a prime target of the British during the War of 1812. In the end, largely because of the town’s stratagem of dimming lights and hanging lanterns in trees, the British failed to destroy the shipyards or cause any significant damage, earning St. Michaels the nickname "The Town That Fooled the British." Just a few years later, in 1818, Talbot County’s most famous native son would be born: Frederick Douglass.
The buildings that comprise the St. Michaels Museum at Mary Square feature an extensive collection of paintings, furnishings, and artifacts that paint a full, vivid picture of nineteenth-century life in the area. At the Chesapeake Bay Maritime Museum, you can immerse yourself in on-the-water experiences, hands-on learning, and top-notch exhibitions. From small boutique shops to a diverse array of restaurants, there’s something for every taste. Among the excellent lodging options is The Old Brick Inn, which offers twenty well-appointed rooms, complimentary breakfast and parking, and an enviable location in the heart of town.
Berlin
Named by USA Today as the Best Town for Shopping in 2018 and 2020, it’s no surprise locals and tourists alike can’t get enough of Berlin. Boasting over 60 retail shops, over fifteen restaurants, music venues, coffee shops, bakeries, galleries, and more, the town’s Main Street is an exciting destination. Moreover, with over 40 structures spanning two centuries of architecture and listed on the National Historic Register, history envelops you. Among these is the Calvin B. Taylor House, which displays local memorabilia and antiques. Moreover, Berlin served as the tree-lined filming location for such films as Tuck Everlasting and Runaway Bride.
Nature lovers will want to visit Maryland’s only oceanfront park, Assateague State Park, for some swimming, kayaking, or fishing. Also, those visiting this year are in for a blast as Berlin hosts over forty free events per year, including a weekly farmers market held downtown, Oktoberfest, and a Christmas parade. Need a place to unwind after the event? Celebrating over 125 years, The Atlantic Hotel delights guests with 15 guestrooms featuring authentic antiques, gracious hospitality, and a historic Bistro Bar.
Annapolis
Dubbed the Sailing Capital of the U.S., Annapolis brims with a rich colonial history and maritime heritage, drawing more than four million people to its shores annually. The small seaport received its current name when Sir Francis Nicholson moved the capital here from St. Mary's City, paying homage to Princess Anne, heir to the throne. A thriving shipping industry brought great wealth to Annapolis, which today has more original 18th-century structures standing than any other city in the United States. Tour and experience fascinating exhibits at the U.S. Naval Academy Museum before visiting St. John’s College, the third oldest college in the country after Harvard University and the College of William and Mary.
Further discover a wealth of historic properties like the William Paca House & Garden, the lavish home of William Paca, signer of the Declaration of Independence. Not to be missed is the mid-1800s Gothic-style St. Mary's Church, which has spectacular arched ceilings and a remarkable wooden altarpiece. After a busy afternoon exploring the shops, art galleries, and restaurants on Main Street, call it a day at the Historic Inns of Annapolis, comprised of three historic buildings that have hosted everyone from prominent state officials to signers of the Declaration of Independence.
Sharpsburg
Just because a town has approximately 600 residents doesn’t mean there’s nothing to do there. In fact, the residential community of Sharpsburg, first settled in 1740, boasts plenty of historic attractions to keep you occupied throughout your weekend getaway. Take the Antietam National Battlefield, the site of a pivotal battle of the Civil War. Visitors can explore this 3,000-acre protected area by foot or car, check out compelling museum exhibits, and pay their respects to the fallen at Antietam National Cemetery.
When George Washington became U.S. President in 1789, he considered the area between Sharpsburg and Shepherdstown as a possible site for the permanent location of the U.S. Capital. To this end, Washington Monument State Park is named for and features the first completed monument to Washington’s memory. Further historic artifacts await travelers at the Sharpsburgh Museum of History, from arithmetic books dating to the 1800s to a metal eagle that flew on the flag pole in town during the Battle of Antietam. Afterward, one can escape to the nearby Greenbrier State Park, which boasts a 42-acre man-made lake and 165 campsites, perfect for a night under the stars.
Chestertown
Serving as Kent County’s seat of government, Chestertown has a storied past dating back to colonial times. It was not only a Royal Port of Entry but also witnessed its own Revolutionary Tea Party in 1774. This charming college town, situated along the banks of the Chester River on Maryland's Eastern Shore, is a mecca for nature lovers and architecture enthusiasts alike. Stroll along the brick-lined sidewalks to explore the town's Historic District, where 18th-century residences and landmarks are beautifully preserved. The scenic streets are dotted with over 200 specialty shops, restaurants, art galleries, and bars, offering something for every visitor.
Year-round events, including the popular Farmers' Market and the Tea Party Festival, keep the town bustling, while more relaxed options can be found at the Eastern Neck National Wildlife Refuge, with its peaceful trails and diverse wildlife. A stop at Washington College, founded in 1782 and named for General George Washington, adds another layer of history to your visit. Before leaving, don't miss the Historical Society of Kent County, which houses illuminating artifacts that provide insight into the area's rich heritage. For a truly immersive experience, stay at the White Swan Tavern, a lovingly restored colonial-era inn that dates back to before 1733 and is located near the waterfront.
Oxford
If a relaxing weekend in a historic and charming waterfront setting sounds appealing, the town of Oxford ought to top your list. Most visitors head straight to ride the Oxford-Bellevue Ferry, a privately owned ferry dating back to 1683, the same year as the town’s own founding, for breathtaking views of the Eastern Shore. Those interested in the past can check out the historic inns dotted around town, such as the 1710 Robert Morris Inn, the oldest full-service inn in America. Four of its 310-year-old rooms were occupied by Founding Father and Revolutionary financier Robert Morris, for whom the property is named; George Washington; and other notable figures. For a learning experience, the Oxford Museum beckons, chronicling more than 300 years of local tales through a wide-ranging collection of memorabilia and artifacts.
On the other hand, families will prefer to stop for a treat at the Scottish Highland Creamery, rated by TripAdvisor as one of the top five ice cream shops in the U.S. Similarly, Oxford Day in late April includes boat rides and a lively parade that anyone will enjoy.
Havre de Grace
With a rich history predating the Civil War era, Havre de Grace offers no shortage of charm and character. Located at the confluence of the Susquehanna River and the Chesapeake Bay, it missed becoming the capital of the United States by just one vote. The town’s storied past left its mark, and iconic landmarks abound. Built in 1827 and listed on the National Register of Historic Places, Concord Point Lighthouse is the oldest publicly accessible lighthouse on the Chesapeake Bay and the second oldest lighthouse in Maryland that still stands. Visit the museum to learn about John O’Neill, who was appointed the first keeper at the lighthouse in recognition of his bravery during the War of 1812. Also popular is the Havre de Grace Maritime Museum, where you’ll gain insight into the region’s maritime heritage
For some shopping, head to Havre de Grace Main Street and grab a souvenir at the Bahoukas Antique Mall, browse fine art galleries, or indulge in Maryland blue crabs at any of a wide range of restaurants. You can also enjoy a picnic at David Craig Park or superb views of the Susquehanna River at Frank J. Hutchins Memorial Park. Book a weekend stay at the Spencer-Silver Mansion, a charming bed and breakfast in the heart of the town’s Historic District.
Easton
Whether you're an avid shopper, nature lover, history buff, or theater enthusiast, Easton has something for everyone. Located in the picturesque Tidewater region along the eastern shore of Chesapeake Bay, this charming town was originally settled by Quakers in 1682 and became an official town in 1710. With its rich history, Easton offers endless opportunities for exploration. Visitors can stroll through the historic downtown area, filled with charming shops and restaurants, or immerse themselves in art and history at local museums. The Academy Art Museum showcases over 1,500 works from the 17th century to today. At the same time, the Talbot Historical Society Museum houses approximately 100,000 vintage photos and artifacts that tell the story of the town's past.
In addition to its cultural attractions, Easton is home to year-round entertainment at the Avalon Theatre and seasonal events at the Talbot County Community Center. For outdoor enthusiasts, the Pickering Creek Audubon Center offers over 400 acres of wildlife sanctuary, perfect for a scenic hike or a peaceful picnic. Easton's Farmers' Market also provides a great opportunity to enjoy local produce and handmade goods. When you're ready to unwind, the Tidewater Inn awaits, offering 86 tastefully decorated rooms, an inviting restaurant, and a full-service luxury spa to ensure a restful stay.
Cambridge
Offering a rich history and plenty of activities to enjoy, you’ll instantly fall in love with this quaint town of roughly 13,000 people in Dorchester County. Founded in 1684 on the banks of the Choptank River, Cambridge is one of the nation's oldest colonial cities, coupling Eastern Shore charm with maritime heritage. Trace the footsteps of Harriet Tubman and learn about her extraordinary life at the Bucktown Store, the Harriet Tubman Museum and Educational Center, and the Harriet Tubman Underground Railroad Visitor Center. From exhibits on her activist work to fun facts about her life, history enthusiasts adore these sports. One can also head to the Richardson Maritime Museum for interesting artifacts and exhibits about the maritime heritage of the Chesapeake Bay.
Home to over 250 species of birds and meandering trails for biking and hiking, the Blackwater National Wildlife Refuge is worth exploring. Another outdoor hotspot is Long Wharf Park, which includes picnic areas, a marina, and the Choptank River Lighthouse. Once you’re ready to call it a night, enjoy a welcome respite at Cambridge House Bed & Breakfast, an 1847 sea captain’s manor conveniently located near the town’s key points of interest.
Solomons Island
If you're seeking a peaceful weekend getaway, Solomons Island in southern Calvert County is a gem that won’t disappoint. The island offers many activities for visitors of all ages. One highlight is the Annmarie Garden Sculpture Park & Arts Center, a 30-acre park brimming with exhibits, vibrant gardens, and play areas for children. To explore the Chesapeake Bay’s natural wonders, stop by the Chesapeake Biological Laboratory Visitors Center for fascinating insights into the area’s ecology.
For history buffs, the Calvert Marine Museum provides a journey through time with its exhibits on paleontology and local marine life. It also offers tours of the Cove Point Lighthouse. Take a leisurely walk along the scenic Solomons Boardwalk, where you can admire views of the Chesapeake Bay and the Patuxent River, before savoring a meal at one of the many waterfront restaurants. Suppose you're looking for accommodations that combine historic charm with modern comfort. In that case, the Solomons Victorian Inn offers beautifully appointed rooms, a cozy library, and the company of two resident cats, ensuring a memorable stay.
Hancock
Hancock, a charming town along the C&O Canal, offers a deep dive into history and nature. The rustic Bowles House, built in the 1780s, stands as a testament to the town’s past, particularly during the canal's development in the 1830s. The house now hosts a visitor center, where you can explore exhibits detailing local canal history. Stop by the Hancock Historical Museum at Town Hall to discover the town's heritage, which showcases artifacts like newspaper archives and memorabilia.
Outdoor enthusiasts will love the Western Maryland Rail Trail, a 28-mile stretch perfect for biking, bird-watching, or simply taking in the scenic beauty from Hancock to Fort Frederick State Park. After the adventures, you can enjoy a cozy place to stay at the 1828 Trail Inn. This hotel features charming accommodations within walking distance of the canal and nearby restaurants.
Maryland’s Enchanting Small Towns Beckon
The small towns of Maryland, imbued with endless history and charm, offer a welcome respite from the fast pace of city life. These charming locales are all about slowing down, savoring the moment, and immersing yourself in the stories of towns you won’t want to leave anytime soon. Whether you’re taking in picture-perfect water views on Solomons Island or ambling through the scenic streets of Chestertown, you’ll be blown away by the timeless charm and beauty of Maryland’s picturesque small towns. No matter which one you plan to visit next, you can rest assured an unforgettable weekend getaway is in store.
