Best Weekend Trips in Maryland 2025

Maryland punches far above its size when it comes to quick escapes. Within a few hours, you can switch from cobblestone harbor towns and seafood shacks to forested mountains, waterfalls, and sandy barrier islands dotted with wild ponies. Because the state sits at the heart of the Mid-Atlantic, weekend trips feel effortless—whether you love history and museums, want a cozy waterfront inn, or prefer a cabin by the lake with a fire pit and a sky full of stars.

In this guide, you’ll find a practical, well-curated list of the best weekend trips in Maryland, organized by travel style. You’ll also get planning tips, budget-friendly advice, and smart suggestions for where to sleep, what to pack, and how to maximize a precious 48–72 hours. By the end, you’ll know exactly where to go and how to make it happen—without the stress.

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Why Take Weekend Trips from Maryland?

Short getaways pay off in big ways. You recharge, explore something new, and avoid the weeks-long planning that a big vacation demands. Because Maryland sits between the Atlantic, the Blue Ridge and Allegheny foothills, and the Washington–Baltimore metro, you have a rare mix of landscapes, cities, and small towns within easy reach.

• Location advantage: Maryland borders Washington, D.C., Pennsylvania, Delaware, Virginia, and West Virginia. That puts numerous scenic byways and historic sites within a few hours’ drive. Yet you rarely need to cross a border to find variety; the state itself offers beaches, bays, mountains, and vibrant neighborhoods.
• Seamless connections: I-95, US-50, and I-70 link major hubs quickly. MARC and Amtrak connect Baltimore, BWI, and D.C. for car-free trips. If you do fly, BWI serves as an efficient base with widespread domestic connections, often at lower fares.
• Low commitment, high reward: A two-night stay gives you enough time to slow down, try local food, and visit a couple of highlights—without sacrificing too much PTO or overspending.

In short, weekend trips from Maryland give you the flexibility to fit travel into real life. You can leave after work on Friday and still feel like you’ve stepped into a different world.

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How to Plan a Weekend Trip from Maryland

Smart planning makes a short trip feel longer. A few choices up front—timing, transport, and a doable itinerary—unlock more time for fun.

Best seasons or times to travel

• Spring (April–June): Wildflowers pop in Western Maryland, and temperatures sit in the comfortable 60s and 70s. It’s prime for hiking Catoctin trails, sailing the Chesapeake, and strolling historic districts before summer crowds.
• Summer (June–August): Beach season brings Ocean City energy and Assateague sunsets. Book early and plan for traffic during peak weekends. Early mornings and late afternoons feel cooler and less crowded.
• Fall (September–November): Leaf-peeping shines in Garrett County (Deep Creek) and along the Catoctin ridge. Harvest festivals, winery events, and crisp hiking weather make it ideal for outdoors and food trips.
• Winter (December–March): Cozy inn season on the Eastern Shore and ski season at Wisp Resort. Holiday markets pop up in Frederick, Annapolis, and Baltimore. Prices often drop midweek.

Transport options (car, train, bus, flights)

• Car: Most destinations in this guide are easiest by car. Traffic ebbs on Friday morning and late evening; consider leaving early or after dinner to dodge congestion. If you need wheels, check weekend deals from BWI or city locations—compact SUVs offer space for gear without guzzling gas.
• Train: MARC runs commuter service on weekdays; it’s useful if you’re extending a Friday or Monday. Amtrak connects Baltimore, BWI, and D.C. with quick travel times—great for an urban-focused Baltimore weekend without parking hassles.
• Bus: BoltBus, Greyhound, Megabus, and FlixBus link Baltimore and D.C. to select Maryland towns and nearby cities inexpensively. For Inner Harbor stays, bus + rideshare works well.
• Flights: BWI sits just south of Baltimore with easy Light Rail access. Although you won’t need to fly for in-state trips, BWI can connect you to farther-flung getaways if you decide to extend your trip beyond Maryland later.

Budget and planning tips

• Set your “one big thing”: Choose one anchor activity (sailing lesson, battlefield tour, aquarium visit, waterfall hike). Plan the rest around it and book it first.
• Book early for popular weekends: Deep Creek and Ocean City fill fast for summer, holiday, and foliage weekends. Waterfront inns on the Eastern Shore often sell out two to three months ahead.
• Mix paid and free: Pair ticketed attractions (aquarium, boat tours, museums) with free hikes, self-guided historic walks, and beach time.
• Eat smarter: Lunchtime prix fixe menus, happy-hour oyster deals, and food halls stretch the budget. Make dinner reservations for high-demand restaurants in Annapolis, Baltimore, St. Michaels, and Frederick.

Packing essentials (with smart add-ons)

• Layers and a light rain shell: Weather can flip near the Bay and in the mountains. A packable rain jacket earns its keep.
• Comfortable walking shoes or trail hikers: Boardwalks, cobblestones, and rocky trails challenge flimsy footwear.
• Daypack with hydration: A 20–25L daypack works for urban sightseeing and short hikes; add a reusable water bottle.
• Sun protection: Sunglasses, hat, and reef-safe sunscreen for beach and boat days.
• Portable charger and small power strip: Keep phones, cameras, and e-readers topped up at old inns with limited outlets.
• Beach or picnic kit: Quick-dry towel, collapsible cooler, and blanket for Assateague, Ocean City, or lakeside sunsets.
• Helpful picks: Consider booking hotels with flexible cancellation on reputable platforms, snagging an America the Beautiful pass if you plan national park sites beyond Maryland, and using a Chesapeake Bay sailing or kayak tour operator with strong reviews for safety gear and local expertise. For gear, a reliable packable rain jacket, moisture-wicking socks, and a compact first-aid kit are easy wins.

Plan purposefully, pack light, and give yourself windows of nothing. That’s how short trips feel like real vacations.

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Best Weekend Trips in Maryland by Category

Romantic Weekend Trips

— Destination 1: St. Michaels and Oxford (Talbot County) —

• Why go: These Eastern Shore towns deliver postcard-perfect marinas, tree-lined streets, and candlelit seafood spots. You’ll find boutique inns, easy bike routes, and sunset sails on the Miles River.
• Top things to do:
  • Cruise the Chesapeake: Book a two-hour sunset sail or a skippered charter; several outfitters depart from St. Michaels Harbor.
  • Chesapeake Bay Maritime Museum: Explore lighthouse history, working boatyards, and rotating exhibits that bring Bay culture to life.
  • Bike to Oxford: Ride the St. Michaels–Oxford loop and cross the Tred Avon River on the tiny Oxford–Bellevue ferry (seasonal), then reward yourself with ice cream at a long-time local favorite in Oxford.
  • Wine and oysters: Taste local pours at nearby wineries and slurp briny oysters at dockside restaurants.
• Travel info: St. Michaels sits about 1.5–2 hours from Baltimore or D.C., traffic permitting. Arrive Friday evening to enjoy a relaxed dinner and a quiet stroll along the harbor.
• Lodging ideas:
  • Inn at Perry Cabin: A waterfront classic with manicured gardens, a spa, and private sailing experiences.
  • St. Michaels Harbour Inn, Marina & Spa: Offers water views and easy marina access.
  • In Oxford, look at waterfront B&Bs for a slower pace.
• Dining tips: Book one special meal (think crab cakes and rockfish) and keep the rest casual. For brunch, find a bakery café on Talbot Street for pastries and coffee.
• Helpful note: Reserve refundable rooms at boutique inns and consider a guided sailing charter for a turnkey experience—gear and safety briefings included.

— Destination 2: Annapolis Historic District —

• Why go: Brick-lined streets, 18th-century rowhouses, and sailboats bobbing on the Severn make Annapolis a timeless romantic pick.
• Top things to do:
  • U.S. Naval Academy tour: Learn the Academy’s history and see the striking Chapel and crypt of John Paul Jones.
  • Sail the Bay: Take a schooner cruise at sunset or a basic sailing lesson for two.
  • Stroll and shop: Window-shop along Maryland Avenue and Main Street, then slip into side alleys for quieter cafes.
  • Waterfront walk: Catch the golden hour from City Dock and grab gelato along Ego Alley.
• Travel info: Annapolis lies about 35–50 minutes from Baltimore or D.C. With weekend events common, secure parking or pick a hotel with a garage.
• Lodging ideas:
  • Annapolis Waterfront Hotel (Autograph Collection): Front-row harbor views.
  • Graduate Annapolis: Stylish rooms near the arts district.
  • Charming B&Bs in Murray Hill for quieter stays.
• Dining tips: Reserve a table at a seafood bistro or Italian spot near the harbor; try a craft cocktail bar later.
• Helpful add-on: Book a sailing cruise in advance during peak spring and fall weekends; consider a flexible cancellation policy to hedge against weather.

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Family-Friendly Weekend Trips

— Destination 1: Ocean City and Assateague Island —

• Why go: The classic Maryland beach meets a wild barrier island where ponies roam. Families can blend boardwalk thrills with nature time just 20 minutes away.
• Top things to do:
  • Ocean City Boardwalk: Ride the Ferris wheel, sample Thrasher’s fries, and play mini-golf or arcades.
  • Beach day: Stake out a spot early, then take a midday break for naps or pool time.
  • Assateague Island National Seashore: Look for wild horses, paddle calm bayside waters, and stay for a pastel sunset. Bring bug spray for summer.
  • Nature programs: Ranger talks and junior ranger activities entertain kids while teaching barrier-island ecology.
• Travel info: From Baltimore or D.C., expect 3–3.5 hours. On peak weekends, beat traffic by leaving before 8 a.m. or after dinner.
• Lodging ideas:
  • Hilton Ocean City Oceanfront Suites and Holiday Inn & Suites: Family-friendly with pools and kitchenettes.
  • Assateague campgrounds: Book months ahead for oceanside tent or RV sites.
  • Condos near North Ocean City reduce noise and simplify parking.
• Dining tips: Food halls and bayside crab houses simplify group meals. Early dinners help avoid lines.
• Gear extras: A collapsible wagon, sun shelter, and rash guards make beach days smoother. Consider a roof box or soft cargo bag if you’re hauling gear in a smaller car.

— Destination 2: Baltimore’s Inner Harbor —

• Why go: A compact waterfront with marquee attractions keeps logistics simple. You can walk between the National Aquarium, Port Discovery Children’s Museum, and the Maryland Science Center.
• Top things to do:
  • National Aquarium: Sharks, jellyfish, and a rainforest exhibit fascinate all ages. Book timed-entry tickets in advance.
  • Historic Ships in Baltimore: Tour the USS Constellation and other vessels; kids love the interactive elements.
  • Port Discovery: Hands-on exhibits for younger children.
  • Camden Yards tour or Orioles game when in season.
  • Neighborhood detours: Little Italy for cannoli, Fells Point for cobblestones and casual eateries.
• Travel info: Trains (Amtrak to Penn Station or MARC to Camden) and Light Rail make car-free weekends easy. If driving, pick a hotel with validated parking.
• Lodging ideas:
  • Royal Sonesta Harbor Court and Renaissance Baltimore Harborplace: Walkable locations with family rooms.
  • Smaller boutique options in Fells Point offer charm and quieter nights.
• Dining tips: Try a harbor-view spot for one meal, then explore food halls or pizza nights to save.
• Helpful add-on: Baltimore attractions often bundle tickets—look for aquarium + museum combos and book online for discounts.

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Adventure & Outdoor Trips

— Destination 1: Deep Creek Lake and Swallow Falls State Park (Garrett County) —

• Why go: Western Maryland’s highlands deliver four-season adventure—boating, ziplining, whitewater rafting, skiing, and some of the state’s best waterfalls.
• Top things to do:
  • Swallow Falls State Park: Hike the 1.5-mile loop to see Muddy Creek Falls, Maryland’s tallest at 53 feet, plus picturesque cascades along the Youghiogheny.
  • Wisp Resort: In winter, ski and snowboard; in warmer months, ride the mountain coaster, try aerial courses, or go disc golfing.
  • Water time: Rent kayaks or a pontoon on Deep Creek Lake for a leisurely afternoon on the water.
  • Adventure sports: Experienced paddlers can time releases at the Adventure Sports Center International’s recirculating whitewater course.
• Travel info: It takes about 3–3.5 hours from Baltimore or D.C. via I-70 and I-68. Weather changes quickly at higher elevations; pack layers.
• Lodging ideas:
  • Lakefront cabins with docks for sunrise coffee and evening fires.
  • Wisp Resort condos for slope access.
  • State park cabins for budget-friendly stays close to trails.
• Dining tips: Stock up at the local market and grill at your rental. Plan one dinner out at a lakeside spot.
• Gear notes: Waterproof hiking shoes, trekking poles for slick trails, and a compact first-aid kit are smart. If you don’t own gear, local outfitters rent kayaks, paddleboards, and winter equipment.

— Destination 2: Catoctin Mountain Park and Cunningham Falls State Park —

• Why go: Rolling ridges, rocky overlooks, and a stunning 78-foot waterfall sit just north of Frederick, which adds breweries and a polished historic core to round out the weekend.
• Top things to do:
  • Hikes: Try Chimney Rock and Wolf Rock for vistas; pair with Cunningham Falls for a scenic loop.
  • Fishing and paddling: The lake at Cunningham Falls suits families and beginners.
  • Scenic drives and picnics: Skyline viewpoints deliver big views with minimal effort.
  • Frederick add-on: After the trails, stroll Carroll Creek Park, browse indie shops, and sample local beers or ice cream.
• Travel info: Catoctin sits about 1–1.5 hours from Baltimore or D.C. Trailheads fill on sunny weekends; arrive by 9 a.m. for easy parking.
• Lodging ideas:
  • Park cabins (Misty Mount) for a rustic feel.
  • Inns and boutique hotels in Frederick for comfort and walkability.
  • Nearby campgrounds for budget stays.
• Dining tips: Grab breakfast burritos before hiking and save a relaxed dinner for Frederick’s Market Street restaurants.
• Helpful add-on: A good daypack, hydration reservoir, and trail map app (download offline) improve safety and comfort.

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Cultural & Historical Trips

— Destination 1: Antietam National Battlefield and Sharpsburg —

• Why go: Antietam preserves the bloodiest single day in American history and offers one of the most well-interpreted Civil War landscapes in the country. The rural setting remains evocative and quiet, ideal for reflection and learning.
• Top things to do:
  • Auto tour: Follow the 11-stop loop with a park map, or book a licensed battlefield guide for context you won’t forget.
  • Hikes: Walk the Cornfield, Dunker Church area, and Burnside Bridge for close-up views.
  • Visitor Center: Exhibits and films set the stage; rangers lead excellent talks.
  • Nearby Sharpsburg and Shepherdstown (across the river in WV) add cafes and antique browsing; stick to Sharpsburg for an all-Maryland itinerary.
• Travel info: From Baltimore or D.C., plan on 1.5–2 hours via I-70. Spring and fall offer the best weather; summer afternoons can be hot in open fields.
• Lodging ideas:
  • Historic B&Bs near Sharpsburg for period ambiance.
  • Hagerstown hotels for chain convenience and quick highway access.
• Dining tips: Pack a picnic for the battlefield, then enjoy a leisurely dinner in a historic tavern nearby.
• Add-on experiences: Pair with the C&O Canal Towpath for a bike ride along the Potomac; bring or rent bikes and helmets.

— Destination 2: St. Mary’s City and Solomons (Southern Maryland) —

• Why go: Maryland’s first capital and a living history museum sit along quiet waterways, while nearby Solomons anchors a compact harbor with the strong Calvert Marine Museum.
• Top things to do:
  • Historic St. Mary’s City: Costumed interpreters, reconstructed buildings, and archaeological sites illuminate early colonial life.
  • Calvert Marine Museum: Meet the famed Drum Point Lighthouse, explore fossil exhibits, and learn Bay ecology.
  • Fossil hunting: Calvert Cliffs State Park offers a scenic hike to the beach; searching for small shark teeth thrills kids and adults.
  • Waterfront walks and sunsets in Solomons.
• Travel info: Expect 1.5–2.5 hours from the Baltimore–D.C. area, depending on starting point and traffic along MD-4.
• Lodging ideas:
  • Waterfront inns and boutique B&Bs in Solomons.
  • Chain hotels in Lexington Park for value and proximity.
• Dining tips: Seek crab soup, rockfish, and seasonal soft-shells at riverside restaurants.
• Helpful add-on: Check museum and living history schedules—seasonal hours vary. Book timed tickets on busy weekends.

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Food & Wine Trips

— Destination 1: Frederick Food Scene and Wine Trail —

• Why go: Frederick blends historic charm with a modern culinary pulse. Within a short drive, scenic vineyards pour Maryland varietals and host live music and food trucks on weekends.
• Top things to do:
  • Downtown tasting tour: Sample small-batch ice cream, bakeries, and chef-driven restaurants around Market Street and Patrick Street.
  • Breweries and distilleries: Flying Dog (check hours) and smaller craft spots pour inventive brews; distilleries offer cocktail flights.
  • Wineries: Linganore Winecellars, Black Ankle Vineyards, and Catoctin Breeze Vineyard deliver countryside views with tastings; check for reservations.
  • Arts and strolls: Public art and the Carroll Creek Promenade set the stage for evening walks.
• Travel info: About 1 hour from Baltimore or D.C. Ride-hailing exists but not reliably for rural wineries; designate a driver or book a tasting tour shuttle.
• Lodging ideas:
  • Boutique hotels and historic inns downtown for walkability.
  • Farm stays outside town for a pastoral vibe.
• Dining tips: Nab a brunch reservation and try a chef’s tasting menu or a farm-to-table dinner one night. Food halls and casual eateries keep costs balanced.
• Helpful add-on: Make winery reservations and check policies on outside food. Bring a small cooler bag for cheese and picnic supplies.

— Destination 2: Sugarloaf Mountain Area and Montgomery County’s Agricultural Reserve —

• Why go: Rolling farmland west of D.C. hides a cluster of wineries, cideries, and breweries near Sugarloaf Mountain. The pairing of short hikes and tastings makes an easy, satisfying weekend.
• Top things to do:
  • Sugarloaf hike: Pick a moderate loop for big views. Go early to find parking.
  • Vineyards and cideries: Sugarloaf Mountain Vineyard, Windridge Vineyards, Rocklands Farm Winery & Market, and Doc Waters Cidery offer lawn seating and live music in season.
  • Farm markets: Stock up on local produce, cheeses, and baked goods for a picnic spread.
  • Historic Poolesville: Stroll a small-town main street and check the schedule for seasonal events.
• Travel info: About 45–75 minutes from D.C. and 1–1.5 hours from Baltimore. Roads are rural; drive carefully at night.
• Lodging ideas:
  • Country inns and B&Bs near Poolesville or Dickerson.
  • Chain hotels in Gaithersburg or Rockville for easy access and points redemption.
• Dining tips: Reserve a late lunch at a winery that hosts food trucks, then grab dinner at a farm-to-table restaurant in nearby towns.
• Helpful add-on: Pack a picnic blanket and reusable wine tumblers. If you prefer not to drive, look for guided wine shuttles operating on weekends.

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Travel Tips for Weekend Trips from Maryland

Make your 2–3 days count with a few proven strategies.

Booking advice

• Reserve early for peak seasons: Summer weekends at Ocean City and fall foliage at Deep Creek sell out fast. Waterfront inns on the Eastern Shore often require two-night minimums.
• Lock in timed-entry tickets: The National Aquarium, popular museums, and some state park attractions use timed entry. Book online to secure your ideal slot and skip long lines.
• Choose flexible rates: Opt for refundable hotel bookings when weather could impact plans, especially for sailing or outdoor-heavy weekends.
• Bundle and save: Look for city passes or attraction bundles in Baltimore. For state parks, consider checking campground availability first, then build your weekend around that anchor.

Safety and accessibility tips

• Weather awareness: Summer storms can blow in quickly along the Bay and in the mountains. Keep an eye on forecasts and park alerts, and have a Plan B (museum, café crawl, or covered market).
• Water safety: Always wear life vests for boating and paddling. Choose outfitters that provide safety briefings and quality equipment.
• Trail basics: Download offline maps, carry water, and stay on marked routes. Black bears live in Western Maryland; follow Leave No Trace guidelines and store food properly when camping.
• Accessibility: Many museums, aquariums, and historic sites offer accessible entrances and programs. Check websites for ADA details, elevator access, and wheelchair rentals.

How to maximize a 2–3 day trip

• Friday evening: Arrive, check in, and take a short sunset walk to get your bearings. Eat near your hotel to avoid late-night logistics.
• Saturday morning anchor: Do your biggest activity first—hike, sail, or flagship museum—before crowds and heat build.
• Saturday afternoon flex: Mix in a second, lighter activity (wine tasting, boat tour, or neighborhood walk). Leave room for a nap or café break.
• Saturday night: Book one memorable dinner, then add a low-key dessert stop or live music.
• Sunday finish strong: Catch a final view—waterfront promenade, lighthouse, or overlook—then visit a small museum or market before heading home.
• Keep travel light: Use a single carry-on or weekender bag per person. Pre-pack a “go kit” with sunscreen, chargers, snacks, and a mini first-aid kit so you can pivot quickly between activities.

Planning helpers

• Lodging platforms with free cancellation let you pounce on good rates without locking you in.
• Car rental weekend specials at BWI and city centers often beat weekday prices; compare compact SUVs for gear space and mileage.
• Regional rail and bus tickets booked ahead can be cheaper and guarantee seats for car-free city weekends.
• Consider travel insurance for prepaid, weather-sensitive experiences like sailing charters or nonrefundable lodges.

With thoughtful planning, Maryland’s compact size becomes your superpower. You can chase ponies on the beach one weekend, toast a vineyard the next, and stand on a Civil War ridge the weekend after that. Pick your style, book the essentials, and let the rest unfold along the water, in the woods, or under the warm glow of historic streets.

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Frequently Asked Questions