Chesapeake Bay Getaway: Baltimore to Ocean City Road Trip

Trip Snapshot

• Distance & Drive Time: Approximately 150 miles (about 3 hours one-way without stops).
• Best Time to Visit: Summer for the full beach experience (June–August), or late spring/early fall for milder weather and fewer crowds.
• Ideal For: Beach lovers, families, wildlife enthusiasts, and anyone looking for scenic bay views and small-town charm.
• Route Summary: Baltimore → I-97 South → US-50 East across the Chesapeake Bay Bridge → Eastern Shore (via US-50/US-301) → Ocean City (Atlantic coast).
• Top Highlights: Driving over the 4.3-mile Chesapeake Bay Bridge with sweeping views, visiting historic Eastern Shore towns like Easton and St. Michaels, seeing wild ponies on the beach at Assateague Island National Seashore, and enjoying the Ocean City boardwalk with its classic treats and amusements.

Route Overview

Leaving Baltimore in the morning, you’ll head south on I-97 toward Annapolis before merging onto US-50 East. In less than an hour, the road rises over the impressive Chesapeake Bay Bridge a 4.3-mile span crossing the bay. Take in panoramic views of sailboats and sparkling blue waters as you drive over (passengers will love the photo ops!). Once you touch down on the Eastern Shore, you enter a different world of rural landscapes and relaxed charm.

Continue east on US-50 through Maryland’s Eastern Shore, a region of farmland, forests, and timeless towns. You might detour into Easton, a quaint historic town just off Route 50, for a cup of coffee or a stroll past brick storefronts and art galleries. If you have extra time, swing down MD-33 to St. Michaels, a picturesque harbor village. Here you can visit the Chesapeake Bay Maritime Museum for a dose of local maritime history and see the boats along the Miles River. Back on the main route, US-50 takes you through communities like Cambridge, where roadside farm stands often sell fresh produce in summer.

As you approach the coast, consider a side trip to Assateague Island National Seashore (via MD-611 before you reach Ocean City). This barrier island is famous for its wild ponies grazing in the dunes and tidal marshes. A short hike from the parking area can lead you to the beach, where you might spot the horses roaming free on the sand — a magical Eastern Shore experience. Finally, continue to the end of US-50 and arrive in Ocean City, MD, marked by the welcome sign and the sight of high-rise hotels. Cruise down Coastal Highway to the inlet: you’ve reached the Atlantic Ocean! Reward yourself with a walk along Ocean City’s bustling boardwalk, the salty breeze, and maybe a creamy soft-serve ice cream as you dip your toes in the sand.

Top Stops & Experiences

• Chesapeake Bay Bridge: Not a stop per se (no pedestrians allowed), but the journey across is a highlight in itself. Marvel at panoramic Chesapeake Bay views from one of the country’s longest over-water spans. (There is a vista point on the eastern side if you want to pull over after the bridge for photos.)
• Easton, MD: A charming small town with colonial history and vibrant Main Street. Stroll Federal-era architecture and boutique shops. Great place for a café break or to browse local art galleries. Check out the Discover Easton visitor site for current events and shop info (e.g. farmers markets, festivals) Easton is often called one of America’s best small towns.
• St. Michaels & Chesapeake Bay Maritime Museum: This postcard-pretty harbor town is worth the slight detour. The Chesapeake Bay Maritime Museum in St. Michaels offers interactive exhibits on bay culture, boat building, and history set on 18 waterfront acres. Walk the docks to see historic Chesapeake buyboats and skipjacks. St. Michaels’ streets are lined with inns, ice-cream shops, and seafood eateries perfect for a leisurely stop.
• Assateague Island National Seashore: A must-do nature detour just before Ocean City. Drive across the short bridge to Assateague Island to find unspoiled beaches and dunes. Look for the famous Assateague wild ponies that roam freely (remember to observe from a distance and secure your food these ponies are crafty!). The National Park Service operates this seashore, and there are visitor centers, walking trails, and picnic areas on the Maryland side. Sun, sand, and wildlife make this a memorable stop outside the bustle of Ocean City.
• Ocean City Boardwalk: The grand finale a 3-mile boardwalk packed with shops, attractions, and eateries. Stroll or bike the wooden planks. Don’t miss treats like Thrasher’s French Fries (an Ocean City tradition since 1929), hot funnel cakes, and Dolle’s saltwater taffy. Trimper’s carousel and arcade games add old-fashioned seaside fun. In summer, the boardwalk is alive with music, street performers, and vacationers enjoying the oceanfront energy.

Where to Eat & Stay

• Eat: For authentic Eastern Shore flavor, stop at a local crab house en route. The Crab Claw in St. Michaels offers waterfront dining with steamed Maryland blue crabs and crab cakes an idyllic lunch spot by the harbor. If you’d rather wait until Ocean City, indulge in a classic boardwalk snack like Thrasher’s fries or Fisher’s popcorn. For dinner, Ocean City has everything from boardwalk pizza to fresh seafood buffets. A local favorite for crabs is Phillips Seafood, a large restaurant near the Boardwalk known for its all-you-can-eat crab feast (come hungry!).
• Stay: Ocean City offers hundreds of lodging options. For easy beach and boardwalk access, consider staying at a hotel or inn in the downtown/Boardwalk area (between the inlet and 10th Street). Many have ocean-view rooms steps from the sand. If you prefer a quieter atmosphere, look at mid-town or North Ocean City where high-rise resorts and condos offer more tranquility. You can find a comprehensive list of accommodations on the official Ocean City tourism site from family-friendly resorts to quaint bayside bed-and-breakfasts. Booking ahead is essential in summer.

Practical Tips

• Bay Bridge Timing: In peak summer months, traffic can back up for miles at the Chesapeake Bay Bridge, especially on Friday afternoons and Saturday mornings. Plan to leave early in the day to beat the rush. If you have an E-ZPass, use the designated lanes for a smoother toll crossing (toll is collected eastbound only, approx. $2.50 for cars).
• Driving & Speed Limits: Once on the Eastern Shore, be mindful of changing speed limits as you approach small towns. Routes like US-50 are straight and rural, but towns often suddenly drop to 25–35 mph and are enforced by local police. Stay within limits to avoid tickets.
• Assateague Detour: If visiting Assateague, bring insect repellent (the marshy areas can have mosquitoes, especially in warm months) and be prepared for a $25 per vehicle entrance fee (valid for 7 days, National Park Service). There are restrooms and cold-water showers at the beach area handy if you take a dip in the ocean.
• Ocean City Parking: In summer, parking near the boardwalk fills up quickly. The inlet lot is the largest (paid hourly or daily). Consider parking further uptown and riding the Ocean City Beach Bus south, or use West Ocean City Park-and-Ride lot with shuttle service to downtown. Once on the boardwalk, a tram also runs the length of it for a small fee a fun way to get around.
• Weather Prep: Summer on the coast is hot and humid pack sunscreen, stay hydrated, and watch for afternoon thunderstorms. If traveling in off-season, note that some boardwalk businesses close or have limited hours beyond Labor Day. However, the drive is still beautiful in fall when foliage on the Eastern Shore turns golden.

Rentals & Logistics

This trip is doable in a day, but feel free to stretch it into a weekend getaway. Reserve the perfect vehicle for your journey something comfortable with AC (Maryland summers are warm) and enough trunk space for beach gear. Most major rental agencies in Baltimore can set you up with a car; if you’re traveling with family or friends, consider a roomy SUV or minivan for comfort. An E-ZPass transponder will be very handy for tolls (Chesapeake Bay Bridge and any others) it works on all Maryland toll facilities. Lastly, download offline maps or ensure your GPS is ready; cell service is generally solid on this route, but can be spotty on Assateague Island. With your car packed and route planned, you’re set to enjoy an iconic Maryland road trip from the Chesapeake Bay to the Atlantic Ocean.