60 days in Eastern Shore Itinerary

Change things up with a short trip to Bordeleau Vineyards & Winery in Eden (about 42 minutes away).

To find photos, more things to do, reviews, and other tourist information, refer to the Crisfield trip itinerary planner.

Calgary, Canada to Crisfield is an approximately 15-hour combination of flight and car. You can also drive. Due to the time zone difference, you'll lose 2 hours traveling from Calgary to Crisfield. Traveling from Calgary in May, expect Crisfield to be a bit warmer, temps between 26°C and 16°C. You'll set off for Assateague Island on the 16th (Tue).

Spend the 17th (Wed) exploring nature at Assateague Island National Seashore.

To find other places to visit, traveler tips, ratings, and other tourist information, read our Assateague Island trip planner.

The Route module can help you plan travel from Crisfield to Assateague Island. In May, daily temperatures in Assateague Island can reach 24°C, while at night they dip to 15°C. On the 26th (Fri), you'll travel to Ocean City.

Venture out of the city with trips to Salisbury (Pemberton Historical Park, Ward Museum of Wildfowl Art, &more). There's much more to do: take a leisurely stroll along Ocean City Boardwalk, examine the collection at Ripley's Believe it or Not! Ocean City, shop like a local with Art League of Ocean City, and stroll around Northside Park.

To see more things to do, other places to visit, ratings, and tourist information, you can read our Ocean City online holiday maker.

The Route module can help you plan travel from Assateague Island to Ocean City. In May, daily temperatures in Ocean City can reach 24°C, while at night they dip to 15°C. Wrap up your sightseeing on the 5th (Mon) to allow time to drive to St. Michaels.

Venture out of the city with trips to Eastern Neck National Wildlife Refuge (in Rock Hall), Queenstown (Queenstown Premium Outlets & Queenstown Harbor Golf) and Cambridge (Christ Episcopal Church, Blackwater National Wildlife Refuge, &more).

To see more things to do, where to stay, and tourist information, read St. Michaels trip planner.

You can drive from Ocean City to St. Michaels in 2 hours. Alternatively, you can drive; or do a combination of shuttle and taxi; or do a combination of bus and taxi. Expect a daytime high around 34°C in June, and nighttime lows around 22°C. Finish your sightseeing early on the 16th (Fri) so you can drive to Stevensville.

Stevensville is known for breweries & distilleries, trails, and wildlife. Your trip includes some of its best attractions: head outdoors with Casey Michelle Charters, learn about winemaking at Mark Cascia Vineyards, hike along Terrapin Nature Park, and see what you can catch with a fishing tour.

For photos, more things to do, reviews, and tourist information, refer to the Stevensville online sightseeing planner.

You can drive from St. Michaels to Stevensville in an hour. Alternatively, you can drive. In June in Stevensville, expect temperatures between 32°C during the day and 22°C at night. On the 25th (Sun), you're off to North East.

Get out of town with these interesting North East side-trips: Earleville (Mount Harmon Plantation & Painted Sky Alpaca Farm & Fiber Mill) and Chestertown (Historical Society of Kent County, Book Plate, &more).

For other places to visit, where to stay, traveler tips, and more tourist information, refer to the North East day trip planning website.

You can drive from Stevensville to North East in 1.5 hours. Alternatively, you can drive. In June in North East, expect temperatures between 32°C during the day and 20°C at night. You'll set off for home on the 5th (Wed).