30 days in Portland & Chestertown Itinerary

30 days in Portland & Chestertown Itinerary

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Route & dates

30 days in Portland & Chestertown Itinerary

Start: Washington DC
+2
train + bus + Fly:  8​h
1
Portland
— 17 nights
Fly + Drive:  12​h
2
Chestertown
— 11 nights
Drive:  1​h 45​min
End: Washington DC

17
nights
Portland

Portland ©
A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Escape the urban bustle at Silver Falls State Park and Mount St. Helens. Discover out-of-the-way places like Wine Tours & Tastings and Fort Vancouver | National Historic Site. Explore the numerous day-trip ideas around Portland: Archery Summit Winery (in Dayton), Evening Land Vineyards (in Dundee) and Evergreen Aviation & Space Museum (in McMinnville). Spend the 16th (Sat) exploring nature at The Lewis And Clark National And State Historical Parks. And it doesn't end there: take a stroll through Northwest (Nob Hill), admire the natural beauty at Portland Japanese Garden, walk around Hoyt Arboretum, and stop by Powell's City of Books.

To find more things to do, photos, ratings, and other tourist information, read our Portland tour itinerary maker tool .

Washington DC to Portland is an approximately 8-hour combination of train and flight. You can also fly; or drive. Due to the time zone difference, you'll gain 3 hours traveling from Washington DC to Portland. Traveling from Washington DC in May, things will get little chillier in Portland: highs are around 70°F and lows about 51°F. Wrap up your sightseeing on the 20th (Wed) to allow time to travel to Chestertown.

Things to do in Portland

Parks Nature Outdoors

Side Trips

Cannon Beach, Oregon City, Cascade Locks, Vancouver, Archery Summit Winery
Highlights from your plan
Hoyt Arboretum ©
Hoyt Arboretum
Mount Hood ©
Mount Hood

11
nights
Chestertown

Chestertown ©
Chestertown is a town in Kent County, Maryland, United States. Visit Calvert Marine Museum and Drum Point Lighthouse and 1879 Hooper Strait Lighthouse for their historical value. Visiting Sunset Beach and Lewes Beach will get you outdoors. Explore Chestertown's surroundings by going to Wye Mills (Old Wye Grist Mill & Old Wye Church), Dover (Air Mobility Command Museum & John Dickinson Plantation) and Blue Earl Brewing Company (in Smyrna). And it doesn't end there: identify plant and animal life at Blackwater National Wildlife Refuge, stroll through The Struble Trail, contemplate the long history of Fort Delaware State Park, and admire the masterpieces at Brandywine River Museum of Art.

To find where to stay, maps, ratings, and other tourist information, read Chestertown online trip itinerary maker .

The Route module can help you plan travel from Portland to Chestertown. The time zone changes from Pacific Standard Time (PST) to Eastern Standard Time (EST), which is usually a 3 hour difference. In May in Chestertown, expect temperatures between 72°F during the day and 55°F at night. Finish up your sightseeing early on the 1st (Mon) so you can go by car back home.

Things to do in Chestertown

Parks Historic Sites Outdoors

Side Trips

Annapolis, St. Michaels, Wye Mills, Stevensville, Dover
Highlights from your plan
Blackwater National Wildlife Refuge ©
Sunset Beach ©
Sunset Beach

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