8 days in Eastern Shore Itinerary

Eschew the tourist crowds and head to Ayers Creek Adventures and Art League of Ocean City. Get in touch with nature at Ocean City Beach and Fishing Charters & Tours. There's lots more to do: look for gifts at The Kite Loft, sample the tasty concoctions at Burley Oak Brewing Company, immerse yourself in nature at Assateague State Park, and see the interesting displays at Ocean City Life-Saving Station Museum.

To see more things to do, other places to visit, and more tourist information, read our Ocean City vacation builder site.

Philadelphia to Ocean City is an approximately 3-hour car ride. You can also drive; or do a combination of flight and bus; or do a combination of train and bus. Expect a bit cooler weather when traveling from Philadelphia in June: highs in Ocean City hover around 79°F, while lows dip to 65°F. Finish your sightseeing early on the 19th (Mon) to allow enough time to travel to Assateague Island.

On the 20th (Tue), explore the wealth of natural beauty at Assateague Island National Seashore.

To find other places to visit, more things to do, where to stay, and tourist information, read our Assateague Island travel planner.

The Route module can help you plan travel from Ocean City to Assateague Island. Expect a daytime high around 79°F in June, and nighttime lows around 65°F. Finish your sightseeing early on the 20th (Tue) to allow enough time to travel to Crisfield.

Start off your visit on the 21st (Wed): head off the coast to Smith Island, take in the waterfront activity at Somers Cove Marina, and then immerse yourself in nature at Janes Island State Park.

To see other places to visit, more things to do, where to stay, and more tourist information, use the Crisfield planner.

The Route module can help you plan travel from Assateague Island to Crisfield. In June, daytime highs in Crisfield are 82°F, while nighttime lows are 66°F. Wrap up your sightseeing on the 21st (Wed) to allow time to travel to Tilghman.

Kick off your visit on the 22nd (Thu): pick up a one of a kind souvenir at Iron Will Woodworks, visit a coastal fixture at 1879 Hooper Strait Lighthouse, then look for gifts at Olivins, and finally head outdoors with Outdoor Activities. Get ready for a full day of sightseeing on the next day: look for all kinds of wild species at Phillips Wharf Environmental Center, then sample the tasty concoctions at Eastern Shore Brewing, then sample the fine beverages at LYON RUM Distillery, and finally indulge in some personalized pampering at some of the best spas.

To find more things to do and more tourist information, refer to the Tilghman planning website.

Explore your travel options from Crisfield to Tilghman with the Route module. In June, daily temperatures in Tilghman can reach 84°F, while at night they dip to 66°F. Finish your sightseeing early on the 23rd (Fri) so you can drive to Stevensville.

On the 24th (Sat), sample the fine beverages at Blackwater Distilling & Tavern, see what you can catch with a fishing tour, then do a tasting at Mark Cascia Vineyards, and finally stroll through Terrapin Nature Park.

To find ratings, where to stay, reviews, and tourist information, use the Stevensville trip itinerary maker website.

Traveling by car from Tilghman to Stevensville takes 1.5 hours. Alternatively, you can drive. June in Stevensville sees daily highs of 82°F and lows of 67°F at night. Wrap up your sightseeing on the 24th (Sat) to allow time to drive back home.