10 Perfect Destinations for a Long Weekend in Maryland
The bonus day of a long weekend provides just enough time to head out on a Maryland adventure without wasting a hard-earned vacation day. A long weekend opens the door to Maryland seaside resorts like Ocean City’s Ashore Resort & Beach Club, boat cruises to Annapolis or Chesapeake City, and quirky attractions like Berlin's Ghost and Mermaid Museums. Spend hours at museums and galleries like Chestertown's RiverArts, or seek out historic landmarks like the Washington Monument in Boonsboro. You can plan an entire getaway around one town or hit a few on an epic road trip with these 10 perfect destinations for a long weekend in Maryland.
Ocean City
With a bevy of accommodations boasting oceanfront views, a nostalgic boardwalk, and foodie delights from carny-style staples to high-end gourmet, Ocean City is an idyllic beach town for long weekend stays. Ashore Resort & Beach Club places oceanfront rooms just steps from the beach and boardwalk. Upscale seafood, a strong wine list, and a relaxed coastal atmosphere ease you into the evening, followed by daiquiris at the hotel’s Wahoo Beach Bar. In the mornings, you can grab a coffee at Ashore Things and head to the beach to laze on the sand or paddle the scenic shoreline to start your day.
Along the boardwalk, Ripley’s Believe It or Not! delivers classic beach-town fun with collections that are equal parts absurd and unsettling. Seacrets: Jamaica, USA is a singular sensation where you can transition from sampling local spirits at Seacret’s Distillery in a speakeasy-inspired tasting room to dinner across the way at their secluded bayfront restaurant and then dance or drink the night away at one of 17 bars. Take part in a century-plus-old boardwalk tradition by indulging in chewy saltwater taffy at Dolle’s Candyland as the ultimate souvenir of your Ocean City weekend.
Annapolis
Boaters consider Annapolis, Maryland, a meeting place where cruising the narrow waterway known as Ego Alley feels like a rite of passage on the East Coast yachting scene. Nothing eases you into your visit to the “America's Sailling Capital” better than a waterfront cruise exploring the crafts docked along Spa Creek and entrancing views of lovely old Annapolis and Eastport homes along the shoreline. On land, red brick sidewalks lead to casual spots like Dry 85, where made-from-scratch comfort food and polished seafood dishes pair with an extensive drinks menu. Check into The Inn On Main, where the renovated rooms in the heart of the action sit above the iconic Chick & Ruth's Delly, where you can find out what has kept this landmark restaurant in business since 1965. Hint: It is likely the crab cakes and waffles.
Annapolis is also all about the arts, with a selection of galleries scattered about town offering hours of “browsability,” including the Elizabeth Myers Mitchell Art Museum set in an award-winning building on the St. John’s College campus. Admire the collection at this nationally accredited visual arts museum, where recent highlights have included works by Henri Matisse and Joan Miró, along with displays featuring Shakespeare’s First Folio. Your evenings include a taste of Annapolis’ performing arts, enjoying a symphonic masterpiece at Maryland Hall.
St. Michaels
Comfortable walking shoes come in handy in St. Michaels, where the name of the game in this 1600s seaside town is aimless wandering to make magical discoveries. Saunter down to the Chesapeake Bay Maritime Museum, where you can watch traditional shipbuilding at the Working Shipyard, take in the views from the Hooper Strait Lighthouse, or hop aboard the historic 1920 "buyboat" Winnie Estelle for a tour. Lodging matters here, and the Inn at Perry Cabin offers Miles River views from its setting along quiet Fogg’s Cove. This 1845charmer feels untouched despite the modern amenities that make your stay more than comfortable. Soothe your weary bones at the inn’s spa with a massage, or unwind in the steam room looking out at the tranquil scenery before dining at the hotel’s Purser’s Pub, and then settle in front of the courtyard firepit for drinks before bed.
Have breakfast at The Galley, where everything is scratch-made, and the atmosphere in the beautifully restored 1806 landmark is warm and stylish. Work off your waffles with a long walk through town, shopping for wares that pique your interest, from olive oil and gourmet vinegar tastings at Olivin’s Tasting Room to bestsellers at Book Hounds. Aspects of the town’s cultural heritage are found among a collection of artifacts at Cannonball House, where a War of 1812 (1813) cannonball lodged in its walls inspired the landmark's name.
Havre de Grace
Baltimoreans can be soaking up the somewhat quirky vibes in Havre de Grace in under an hour, leaving more than enough time to make the most of your long weekend. The wraparound porch and sycamore-lined grounds of The Spencer Silver Mansion signal one of the area’s most inviting bed-and-breakfasts in Harford County. The Havre de Grace Decoy Museum houses one of the finest collections of working and decorative Chesapeake Bay decoys, a centuries-old art form tied to the area's “waterfowling” heritage. Dine on fresher-than-fresh Maryland Blue Crab at Water Street Seafood, where unrushed service allows you to sip your wine and savor every bite of the elegant dishes that are well worth the wait.
Your complimentary breakfast in the cozy dining room at your B&B is the perfect start to your day, discovering weird and eclectic attractions like Bahoukas Antique Mall and the Beer MuZeum. The circa 1880 historic building is packed to the rafters with “whatever you’re looking for,” with discoveries that keep you searching and gasping with delight for hours. That eclectic spirit continues at Washington Street Books Entertainment Museum, a book, music, and comic shop that doubles as a museum of Hollywood costumes, props, and scripts.
Chestertown
This Chester River destination is made for art lovers with its impressive Arts & Entertainment district in the heart of its 18th-century downtown. Expressive collections of original works are found throughout Chestertown's studios and galleries, ranging from colorful handblown glass at Hegland Glass to thought-provoking exhibits at RiverArts, where local artists' works span diverse media and intriguing themes. Washington College's Kohl Gallery takes you through the archives, installations, and exhibits at one of America’s oldest liberal arts colleges, where immersive experiences often combine visual and performing arts, and items from personal collections range from the iconic cat blanket of renowned author Sophie Kerr to snapshots from the life of politician Louis Goldstein. You can also catch a live performance at the college's Norman James Theatre or attend showings as part of their Film Series.
Make a point of having at least one meal at The Kitchen at the Imperial, where comforting dishes focus on Maryland-sourced ingredients and new experiences in flavor. Comfy stays at The White Swan Tavern have been a Chestertown tradition since before the Revolutionary War, where you can find elegant accommodations beneath exposed beams and a satisfying breakfast to sustain your weekend wanderings.
Berlin
If you are interested in the eerie or curious, Berlin's access to an island of feral ponies and oddball museums is sure to raise an eyebrow or two. Assateague Island’s wild ponies are an enigma; local folklore says they survived a shipwreck, but no records confirm it. Their ancestors still gallop along the shoreline, feed on beach vegetation, and move between the beach, marshes, and wooded areas. The National Seashore’s wind-swept beaches, sheltered bays, and maritime forests are made for days of outdoor adventure hiking, fishing, kayaking, or snapping photos of the famous ponies. The Ghost Museum takes a different approach, examining ideas of the afterlife, reported ghost sightings, and paranormal history. Continue your investigation into otherworldly creatures at the Mermaid Museum, where mermaid sightings are recorded back to the 1st century C.E. and the mermaid myth is explained through a collection of curious artifacts.
Berlin's food and drink scene delivers at spots like Forgotten Fifty Distilling, where cuisine and spirits are an art form. Handcrafted vodka and gin spike creative libations on the cocktail menu, paired beautifully with elevated comfort foods like shrimp ‘n grits, crab cakes, and fried chicken. Begin and end your days at the circa 1895 Hotel Atlantic, where guest rooms capture period authenticity, and the vintage bar continues a century-plus-old tradition of serving drinks and light fare in the afternoon.
Chesapeake City
Chesapeake City is Maryland’s only town on a working commercial canal, where boaters find a welcome stop when traveling the Atlantic Intracoastal Waterway. The docks are busy with summer visitors who love being within walking distance of downtown and riding the Chesapeake City Ferry connecting the north and south sides of town. The deep-water marina at Schaefer’s Canal House is a popular waypoint for boaters, who can find a slip for the night, join locals for drinks at the expansive deck at the Lighthouse Bar, and have a first-class meal at the marina's restaurant.
Bikers and hikers take in the scenery along the 14.5-mile multi-purpose C&D Canal trail system, where anglers fishing along the waterway are a common sight, and joggers occasionally share the trail with horseback riders. After a day on the trail, quench your thirst at Bayheads® Brewing Company, where the taproom serves up their brand of craft beers along with a selection of assorted tipples, and the bartenders are happy to order in lunch from Chesapeake Inn Restaurant and Marina for hungry guests. Tours and wine tasting at the pastoral acreage overlooking the river at Bohemia Manor Farm take you through the winemaking process, followed by a chef-prepared gastro experience at Bohemia Manor Farm’s restaurant and an upscale stay in the private quarters of the Vintner’s Cottage.
Easton
In Easton, parkland and art intersect, turning a simple hike into an open-air gallery experience. Adkins Arboretum’s natural settings and cultivated gardens are part of one of the few arboretums or public gardens with a sole focus on nurturing the native flora of the Mid-Atlantic coastal plain. Wander the trails to discover trees and shrubs, seasonal wildflowers, grasses, and ferns, or watch painters capture the beauty of the landscape at a Plein Air Art event. Fiber art creations adorn dormant trees in colorful wraps at the annual Adkins Arboretum's "Yarnstorming" exhibit before the buds appear in spring. Follow over 4 miles of trails at the Pickering Creek Audubon Center to discover Pollinator and Herb gardens, or paddle the creek by canoe or kayak. Look for murals painted on farm buildings and boathouses and hidden in the garden, and birdwatch from viewing platforms and docks found along the biodiverse trails.
Perfect your swing at Hog Neck Golf Course on its well-maintained greens. Spend your days in the great outdoors and evenings in the lap of luxury at the historic Tidewater Inn, where luxe period rooms and delectable dining at Hunter’s Tavern await.
Boonsboro
Traveling inland, Boonsboro appeals to history lovers, anchored by South Mountain and multiple state parks tied to key moments in the past. South Mountain State Park is part of the Blue Ridge Mountain Range, where the Battle of South Mountain was fought in 1862. Quirauk Mountain is the tallest peak near this stretch of the Appalachian National Scenic Trail, sitting at 2,145 feet, and several scenic lookouts afford sweeping views of the expansive parkland from less strenuous heights. Two monuments near town include the War Correspondents Memorial Arch at Gathland State Park and the Washington Monument at Washington Monument State Park.
In town, get your fill of small-batch craft beers and pizza at Il Forno Vanish, or take a walking tour of the most notable 18th- and 19th-century landmarks, from one of the town’s oldest log buildings dating back to 1802, to the first stone façade circa 1796 reflecting the French Second Empire style at the former Eagle Hotel. Now a boutique charmer, the InnBoonsboro on the Square is just what you need to spoil yourself in themed rooms inspired by silver screen sensations Nick & Nora, Shakespeare, Jane Austen, and unexpected romances like The Princess Bride. A 2-course breakfast provides sustenance to tackle the highest peak at South Mountain or complete the entire walking tour around town.
Cumberland
The cityscape of this arts community is spiked with church steeples set against the Ridge-and-Valley Appalachians and hugged by a gentle curve in the Potomac River. Cumberland is a fall destination best enjoyed when the hills burst into autumnal colors. Art makes its mark on walls throughout town, from the 100-foot three-dimensional Skipper's View that changes when viewed from different angles to the We Are Swept mural on Canal Place Heritage Park. The C. William Gilchrist Gallery and Museum is housed in an early 19th-century Federal mansion, where six renovated galleries, collections, visiting exhibitors, and landscaped gardens introduce visitors to a wide range of media, and scheduled lectures and performances take you from the visual to the performing arts.
Hiking or biking the Great Allegheny Passage trail takes you along one of National Geographic’s "Top Fall Trips In The World." In winter, snow-covered trails offer a quieter experience best suited to cross-country skiing or snowshoeing. Recover from your adventures at Rocky Gap Casino, Resort & Golf with a spa massage, and dine at the Lakeside Grille overlooking Rocky Gap State Park before retiring to your room and enjoying private views of Lake Habeeb.
Year-Round Long Weekend Getaways in Maryland
Although boaters and beach lovers plan their trips around summer celebrations for Ocean City, Annapolis, and Chesapeake City, there is no need to wait for warm weather for your getaway. Cozy inns make natural base camps for cold-weather escapes. From fall colors and cross-country skiing in Cumberland to rainy-day-friendly museums and galleries in Havre de Grace, Chestertown, and Berlin, these 10 perfect destinations for a long weekend in Maryland welcome travelers year-round.
