60 days in Maine & Oregon Itinerary

60 days in Maine & Oregon Itinerary

Created using Inspirock United States travel route planner

Make it your trip
Fly
1
Portland
— 7 nights
Drive
2
Camden
— 7 nights
Drive
3
Bar Harbor, Mount Desert Island
— 8 nights
Fly
4
Hood River
— 7 nights
Drive
5
Portland
— 8 nights
Drive
6
Cannon Beach
— 7 nights
Drive
7
Newport
— 7 nights
Drive
8
Bend
— 8 nights
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Portland

— 7 nights

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Change things up with these side-trips from Portland: York (Old Gaol & Nubble Lighthouse), Tributary Brewing (in Kittery) and Ogunquit (Ogunquit Museum of American Art, Perkins Cove, &more). There's lots more to do: learn insider's secrets on The Maine Brew Bus, explore the landscape on two wheels at Eastern Promenade Trail, enjoy the sea views from Portland Head Light, and walk around Fort Williams Park.

To find photos, ratings, maps, and other tourist information, you can read our Portland trip planner.

New York City to Portland is an approximately 3-hour flight. You can also drive; or take a bus. In May, Portland is slightly colder than New York City - with highs of 64°F and lows of 45°F. Finish your sightseeing early on the 8th (Sat) to allow enough time to drive to Camden.

Things to do in Portland

Parks · Historic Sites · Outdoors · Breweries & Distilleries

Side Trips

Camden

— 7 nights
Get out of town with these interesting Camden side-trips: Pemaquid Point Lighthouse (in Bristol), Glidden Point Oyster Farms (in Edgecomb) and Maine State Museum (in Augusta).

For maps, ratings, and more tourist information, read Camden itinerary planning site.

You can drive from Portland to Camden in 2 hours. Alternatively, you can take a bus. Traveling from Portland in May, you will find days in Camden are little chillier (59°F), and nights are about the same (43°F). Wrap up your sightseeing on the 15th (Sat) early enough to drive to Bar Harbor.

Things to do in Camden

Parks · Museums · Outdoors · Nature

Side Trips

Bar Harbor, Mount Desert Island

— 8 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Change things up with these side-trips from Bar Harbor: Winter Harbor (Whopaints Gallery & Winter Harbor 5&10), Bangor (Cole Land Transportation Museum & Paul Bunyan Statue) and Chipman's Wharf (in Milbridge). There's still lots to do: look for all kinds of wild species at Shore Path, take your sightseeing to a higher altitude at Cadillac Mountain, don't miss a visit to Land Bridge to Bar Island, and take a tour by water with Boat Tours & Water Sports.

For reviews, where to stay, maps, and other tourist information, go to the Bar Harbor travel route planner.

You can drive from Camden to Bar Harbor in 2 hours. Alternatively, you can take a bus. In May, daily temperatures in Bar Harbor can reach 60°F, while at night they dip to 43°F. Wrap up your sightseeing by early afternoon on the 23rd (Sun) to allow enough time to fly to Hood River.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trips

Hood River

— 7 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Explore Hood River's surroundings by going to Timberline Lodge and Ski Area (in Timberline Lodge), Cascade Locks (Bonneville Lock & Dam & Eagle Creek Trail) and Summit Ski Area (in Government Camp). And it doesn't end there: explore the activities along Columbia River Gorge National Scenic Area, snap pictures at Bridge of the Gods, take a memorable drive along Hood River County Fruit Loop, and contemplate the geological forces at Mount Hood.

To find reviews, traveler tips, maps, and more tourist information, read our Hood River trip itinerary maker tool.

Traveling by flight from Bar Harbor to Hood River takes 10 hours. Alternatively, you can drive; or do a combination of bus and train. Due to the time zone difference, you'll gain 3 hours traveling from Bar Harbor to Hood River. Expect a bit warmer temperatures when traveling from Bar Harbor in May; daily highs in Hood River reach 67°F and lows reach 49°F. Wrap up your sightseeing on the 30th (Sun) early enough to drive to Portland.

Things to do in Hood River

Parks · Nature · Outdoors · Wildlife

Side Trips

Portland

— 8 nights

City of Roses

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.
Explore the numerous day-trip ideas around Portland: Adelsheim Vineyard (in Newberg), Willamette Valley Vineyards (in Turner) and Salem (Bush Barn Art Center & Schreiner's Iris Gardens). The adventure continues: admire the natural beauty at Portland Japanese Garden, admire the landmark architecture of Pittock Mansion, meet the residents at Oregon Zoo, and get outside with Portland Timbers.

To see photos, ratings, other places to visit, and more tourist information, read our Portland trip itinerary website.

Traveling by car from Hood River to Portland takes 1.5 hours. Alternatively, you can take a bus; or take a train. In May, daytime highs in Portland are 70°F, while nighttime lows are 51°F. Cap off your sightseeing on the 7th (Mon) early enough to go by car to Cannon Beach.

Things to do in Portland

Parks · Museums · Outdoors · Tours

Side Trips

Cannon Beach

— 7 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. Change things up with these side-trips from Cannon Beach: Kilchis Point Reserve (in Bay City), Tillamook (Tillamook Air Museum & Cape Lookout State Park) and Garibaldi Museum (in Garibaldi). There's still lots to do: admire the majestic nature at Ecola State Park, stroll through Cannon Beach, view the masterpieces at Icefire Glassworks, and look for gifts at Cannon Beach Bookstore.

To find more things to do, ratings, where to stay, and tourist information, refer to the Cannon Beach online road trip planner.

Drive from Portland to Cannon Beach in 1.5 hours. Alternatively, you can take a bus. Expect slightly colder weather when traveling from Portland in June: highs in Cannon Beach hover around 66°F, while lows dip to 52°F. Wrap up your sightseeing on the 14th (Mon) early enough to drive to Newport.

Things to do in Cannon Beach

Parks · Nature · Outdoors · Beaches

Side Trips

Newport

— 7 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Venture out of the city with trips to Lincoln City (Connie Hansen Garden Conservancy, Lincoln City Glass Center, &more), Florence (Strawberry Hill Wayside, Sea Lion Caves, &more) and Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Yachats coastline). Next up on the itinerary: look for all kinds of wild species at Yaquina Head Outstanding Natural Area, cruise along Oregon Coast Hwy, engage your brain at Hatfield Marine Science Center, and admire the majestic nature at Yaquina Bay State Recreation Area.

To see other places to visit, maps, photos, and other tourist information, read Newport tour planner.

You can drive from Cannon Beach to Newport in 3 hours. Alternatively, you can take a bus. When traveling from Cannon Beach in June, plan for a bit cooler days and about the same nights in Newport: temperatures range from 61°F by day to 48°F at night. Finish your sightseeing early on the 21st (Mon) to allow enough time to drive to Bend.

Things to do in Newport

Parks · Outdoors · Nature · Museums

Side Trips

Bend

— 8 nights
An old logging town at the crux of the high desert and ponderosa pine forest, Bend melds a love of the outdoors with cosmopolitan flair.
You'll find plenty of places to visit near Bend: Sisters (McKenzie Pass-Santiam Pass loop, Sahalie and Koosah Falls, &more), Crooked River Ranch Golf Course (in Crooked River Ranch) and Smith Rock State Park (in Redmond). There's still lots to do: examine the collection at High Desert Museum, look and learn at Oregon Observatory, take a memorable tour with Tours, and take in the pleasant sights at Deschutes River Trail.

For where to stay, more things to do, reviews, and more tourist information, use the Bend trip planner.

Traveling by car from Newport to Bend takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. Traveling from Newport in June, expect nights in Bend to be about the same, around 45°F, while days are somewhat warmer, around 75°F. Cap off your sightseeing on the 29th (Tue) early enough to catch the flight back home.

Things to do in Bend

Parks · Outdoors · Nature · Museums

Side Trips

Maine travel guide

4.6
Beaches · Lighthouses · Mountains
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.

Oregon travel guide

4.4
Gardens · State Parks · Specialty Museums
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.