4 days in Eastern Shore Itinerary

4 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore trip itinerary builder

Plan created by another user. Make it yours
Ocean City
— 2 nights
St. Michaels
— 1 night


Ocean City

Ocean City ©
One of the country's favorite vacation resorts, Ocean City draws nearly 8 million visitors annually with its oceanfront boardwalk, clean beaches, and amusement parks.
Explore Ocean City's surroundings by going to Chesapeake Ghost Walks (in Marion Station) and Janes Island State Park (in Crisfield). The adventure continues: kick back and relax at Ocean City Beach, walk around Northside Park, let your taste buds guide you at OC Foodie Tour, and immerse yourself in nature at Assateague State Park.

To see more things to do, where to stay, and tourist information, you can read our Ocean City trip itinerary planning tool.

Washington DC to Ocean City is an approximately 3-hour car ride. You can also take a bus; or do a combination of train and bus. In October, plan for daily highs up to 69°F, and evening lows to 53°F. Wrap up your sightseeing on the 27th (Tue) early enough to drive to St. Michaels.

Things to do in Ocean City

Tours · Parks · Outdoors

Side Trips

Berlin, Chesapeake Ghost Walks, Janes Island State Park
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Chesapeake Ghost Walks ©
Chesapeake Ghost Walks

St. Michaels

St. Michaels ©
Kick off your visit on the 28th (Wed): see the interesting displays at Chesapeake Bay Maritime Museum, then take a tour by water with Boat Tours & Water Sports, then look for gifts at The Candleberry Shoppe, and finally brush up on your knowledge of spirits at Lyon Rum Distillery & Tasting Room.

To see photos, reviews, traveler tips, and other tourist information, read our St. Michaels trip itinerary builder tool.

You can drive from Ocean City to St. Michaels in 2 hours. Alternatively, you can do a combination of bus and taxi. In October, plan for daily highs up to 70°F, and evening lows to 53°F. Cap off your sightseeing on the 28th (Wed) early enough to go by car back home.

Things to do in St. Michaels

Museums · Shopping · Outdoors
Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Boat Tours & Water Sports
Lyon Rum Distillery & Tasting Room ©
Lyon Rum Distillery & Tasting Room