60 days in Eastern Shore Itinerary

60 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore trip planner
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Make it your trip
Fly to Philadelphia International Airport, Drive to Elkton
1
Elkton
— 9 nights
Drive
2
Stevensville, Kent Island
— 10 nights
Drive
3
Ocean City
— 12 nights
Unknown
4
Assateague Island
— 9 nights
Unknown
5
Crisfield
— 9 nights
Drive
6
St. Michaels
— 10 nights
Drive to Baltimore/Washington International Thurgood Marshall Airport, Fly to Toronto

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Elkton — 9 nights

The town of Elkton is the county seat of Cecil County, Maryland, United States. Venture out of the city with trips to Chestertown (Book Plate, Sultana Education Foundation, &more) and Earleville (Mount Harmon Plantation & Painted Sky Alpaca Farm & Fiber Mill). There's still lots to do: indulge your senses at M/V Bay Breeze of Chesapeake City, snap pictures at Gilpin's Falls Covered Bridge, relax in the rural setting at Milburn Orchards, and don't miss a visit to Historical Society of Cecil County.

Plan a trip to Elkton easily and quickly by telling Inspirock to suggest an itinerary.

Toronto, Canada to Elkton is an approximately 6.5-hour combination of flight and car. You can also drive. When traveling from Toronto in August, plan for a bit warmer days and about the same nights in Elkton: temperatures range from 34°C by day to 22°C at night. Wrap up your sightseeing on the 10th (Wed) early enough to drive to Stevensville.
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Parks · Museums · Nature · Wineries
Side Trips

Stevensville, Kent Island — 10 nights

Stevensville is a census-designated place (CDP) in Queen Anne's County, Maryland, and is the county's most populous place among both CDPs and municipalities. Stevensville is known for breweries & distilleries, trails, and wildlife. Your trip includes some of its best attractions: get outside with Lead Dog Charters, sample the fine beverages at Blackwater Distilling & Tavern, learn about winemaking at Mark Cascia Vineyards, and trek along Terrapin Nature Park.

To see maps, other places to visit, and tourist information, read Stevensville day trip planning tool.

Getting from Elkton to Stevensville by car takes about 1.5 hours. In August, daily temperatures in Stevensville can reach 32°C, while at night they dip to 24°C. On the 20th (Sat), you'll travel to Ocean City.
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Outdoors · Wildlife · Tours · Parks

Ocean City — 12 nights

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.
Change things up with these side-trips from Ocean City: Salisbury (Salisbury Zoo, Ben's Red Swings Community Playground, &more). There's still lots to do: take a leisurely stroll along Ocean City Boardwalk, walk around Northside Park, get outside with Outdoor Activities, and find something for the whole family at Trimper's Rides and Amusement Park.

For photos, more things to do, reviews, and tourist information, refer to the Ocean City online tour itinerary planner.

Drive from Stevensville to Ocean City in 2 hours. Alternatively, you can drive. Expect a daytime high around 32°C in August, and nighttime lows around 22°C. Wrap up your sightseeing on the 1st (Thu) to allow time to travel to Assateague Island.
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Parks · Outdoors · Theme Parks · Golf
Side Trips

Assateague Island — 9 nights

Spend the 2nd (Fri) exploring nature at Assateague Island National Seashore.

For ratings, more things to do, other places to visit, and more tourist information, refer to the Assateague Island trip itinerary planning tool.

Explore your travel options from Ocean City to Assateague Island with the Route module. September in Assateague Island sees daily highs of 30°C and lows of 20°C at night. On the 10th (Sat), you're off to Crisfield.
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Nature · Wildlife · Parks
Highlights from your trip

Crisfield — 9 nights

Crisfield is a city in Somerset County, Maryland, United States, located on the Tangier Sound, an arm of the Chesapeake Bay. Change things up with a short trip to Bordeleau Vineyards & Winery in Eden (about 42 minutes away). There's lots more to do: immerse yourself in nature at Janes Island State Park, examine the collection at Crisfield Heritage Foundation, take in the waterfront activity at Somers Cove Marina, and step off the mainland to explore Smith Island.

To see where to stay, reviews, ratings, and tourist information, you can read our Crisfield online vacation planner.

Use the Route module to find suitable travel options from Assateague Island to Crisfield. Expect a daytime high around 31°C in September, and nighttime lows around 20°C. On the 19th (Mon), you'll travel to St. Michaels.
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Parks · Nature · Museums · Wineries
Side Trip

St. Michaels — 10 nights

Change things up with these side-trips from St. Michaels: Cambridge (Harriet Tubman Museum and Educational Center, Blackwater National Wildlife Refuge, &more) and Eastern Neck National Wildlife Refuge (in Rock Hall).

To see other places to visit, reviews, and other tourist information, read St. Michaels trip itinerary planning tool.

You can drive from Crisfield to St. Michaels in 2 hours. In September, daytime highs in St. Michaels are 31°C, while nighttime lows are 19°C. Wrap up your sightseeing on the 29th (Thu) to allow time to travel back home.
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Museums · Parks · Wildlife · Historic Sites
Side Trips