60 days in Maine Itinerary

60 days in Maine Itinerary

Created using Inspirock Maine holiday builder
Make it your trip
Fly
1
York
— 8 nights
Drive
2
Scarborough
— 8 nights
Drive
3
Carrabassett Valley
— 7 nights
Drive
4
Bar Harbor, Mount Desert Island
— 9 nights
Unknown
5
Deer Isle
— 7 nights
Drive
6
Thomaston
— 7 nights
Drive
7
Phippsburg
— 7 nights
Drive
8
Bailey Island
— 6 nights
Drive

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York — 8 nights

York is a town in York County, Maine, United States, near the southern tip of the state. Shop till you drop at Stonewall Kitchen and Spoiled Rotten. Explore hidden gems such as Long Sands Beach and Kittery Trading Post. Venture out of the city with trips to Innisfree Bookshop (in Meredith), Holderness (Squam Lakes Natural Science Center & West Rattlesnake Mountain) and Gilford (Beans & Greens Farm & Gunstock Mountain Resort). Next up on the itinerary: look for gifts at Yummies Candy and Nuts, enjoy the sand and surf at Drakes Island Beach, get some fabulous bargains at Tanger Outlets Tilton, and appreciate the extensive heritage of Mount Agamenticus.

For where to stay, other places to visit, ratings, and tourist information, you can read our York online attractions planner.

Louisville to York is an approximately 5.5-hour flight. You can also drive; or do a combination of bus and taxi. Traveling from Louisville in May, things will get little chillier in York: highs are around 66°F and lows about 47°F. Finish your sightseeing early on the 9th (Thu) to allow enough time to drive to Scarborough.
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Outdoors · Parks · Beaches · Shopping
Side Trips

Scarborough — 8 nights

Scarborough is a town in Cumberland County on the southern coast of the U.S. state of Maine. You'll discover tucked-away gems like Pine Point Beach and Higgins Beach. For shopping fun, head to Len Libby Chocolates or The Old Country Store. You'll find plenty of places to visit near Scarborough: Oxford Casino (in Oxford), Lincoln (Seven Birches Winery & Flume Gorge) and Sap House Meadery (in Center Ossipee). And it doesn't end there: sample the tasty concoctions at Allagash Brewing Company, enjoy some music at Children's Museum and Theatre of Maine, admire the sheer force of Glen Ellis Falls, and buy something for everyone on your list at Maine Mall.

To see more things to do, maps, and other tourist information, use the Scarborough tour planner.

Traveling by car from York to Scarborough takes an hour. In May in Scarborough, expect temperatures between 64°F during the day and 45°F at night. Wrap up your sightseeing on the 17th (Fri) early enough to drive to Carrabassett Valley.
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Outdoors · Parks · Shopping · Nature
Side Trips

Carrabassett Valley — 7 nights

Carrabassett Valley is a town in Franklin County, Maine, United States. Head to L.L. Cote Sports Center and Moosehead Lake Indian Store at Kamp Kampfor plenty of shopping. You'll discover tucked-away gems like Sugarloaf Mountain and Sugarloaf Golf Club. Explore the numerous day-trip ideas around Carrabassett Valley: Belgrade Lakes Golf Club (in Belgrade Lakes), Newry (Sunday River Country Club & Step Falls Preserve Hiking Trail) and Skowhegan (Bigelow Brewing Company & Margaret Chase Smith Library). There's much more to do: cruise along Height of Land, snap pictures at Sunday River Covered Bridge, look for gifts at First Lake General Store, and explore the activities along Prong Pond.

To see ratings, maps, more things to do, and tourist information, go to the Carrabassett Valley day trip planning site.

You can drive from Scarborough to Carrabassett Valley in 3 hours. In May in Carrabassett Valley, expect temperatures between 62°F during the day and 43°F at night. Finish up your sightseeing early on the 24th (Fri) so you can go by car to Bar Harbor.
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Parks · Nature · Outdoors · Golf
Side Trips

Bar Harbor, Mount Desert Island — 9 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. You'll explore the less-touristy side of things at Egg Rock Light and Pirate's Cove Miniature Golf. For shopping fun, head to A Little Mad or The Rock & Art Shop. Get out of town with these interesting Bar Harbor side-trips: US Bells (in Prospect Harbor), Winter Harbor (Winter Harbor 5&10, Schoodic Mountain, &more) and Bartlett Maine Estate Winery (in Gouldsboro). Next up on the itinerary: hike along Bar Island Trails, look for gifts at The Acadia Country Store, hunt for treasures at Mount Desert Island Farmers Markets, and stroll around Agamont Park.

To find reviews, other places to visit, ratings, and other tourist information, read our Bar Harbor online travel planner.

Getting from Carrabassett Valley to Bar Harbor by car takes about 3.5 hours. In May, daily temperatures in Bar Harbor can reach 60°F, while at night they dip to 43°F. Wrap up your sightseeing on the 2nd (Sun) early enough to travel to Deer Isle.
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Parks · Outdoors · Shopping · Trails
Side Trips

Deer Isle — 7 nights

Deer Isle is a town in Hancock County, Maine, United States. You'll explore the less-touristy side of things at Stonington Village and Deer Isle Village. Next up on the itinerary: take in the exciting artwork at Nervous Nellie's Jams and Jellies, identify plant and animal life at Barred Island Preserve, hike along Edgar M. Tennis Preserve, and examine the collection at Deer Isle-Stonington Historical Society.

To see maps, reviews, where to stay, and tourist information, go to the Deer Isle trip planner.

Getting from Bar Harbor to Deer Isle by journey takes about 1.5 hours. In June, plan for daily highs up to 68°F, and evening lows to 52°F. On the 9th (Sun), you'll travel to Thomaston.
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Parks · Wildlife · Museums · Trails

Thomaston — 7 nights

You'll discover tucked-away gems like Cellardoor Winery and Maine State Prison Store. Shop till you drop at Owls Head Lighthouse and Granite Hall Store. Explore Thomaston's surroundings by going to Morse's Sauerkraut (in Waldoboro), Union (Sweetgrass Farm Winery and Distillery & Savage Oakes Vineyard and Winery) and Liberty Tool Company (in Liberty).

To find other places to visit, ratings, where to stay, and tourist information, go to the Thomaston trip planner.

You can drive from Deer Isle to Thomaston in 2 hours. In June, daytime highs in Thomaston are 68°F, while nighttime lows are 51°F. Cap off your sightseeing on the 16th (Sun) early enough to go by car to Phippsburg.
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Parks · Shopping · Museums · Outdoors
Side Trips

Phippsburg — 7 nights

Phippsburg is a town in Sagadahoc County, Maine, United States, on the west side of the mouth of the Kennebec River. Step off the beaten path and head to Popham Beach State Park and Pemaquid Point Lighthouse. Shop till you drop at Freeport Shopping Outlets and Wilbur's of Maine Chocolate Confections. Explore the numerous day-trip ideas around Phippsburg: Tandem Glass Gallery & Studio (in Dresden), Ricker's Hard Cider (in Turner) and Lewiston (Veteran's Park, Basilica of Saints Peter and Paul, &more). Next up on the itinerary: immerse yourself in nature at Reid State Park, sample the tasty concoctions at Maine Beer Company, stop by Scrummy Afters Candy Shoppe, and browse the eclectic array of goods at Montsweag Flea Market.

For maps, photos, other places to visit, and tourist information, refer to the Phippsburg trip app.

You can drive from Thomaston to Phippsburg in 1.5 hours. June in Phippsburg sees daily highs of 73°F and lows of 52°F at night. Finish your sightseeing early on the 23rd (Sun) to allow enough time to drive to Bailey Island.
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Parks · Shopping · Outdoors · Wildlife
Side Trips

Bailey Island — 6 nights

Discover out-of-the-way places like Land's End Gift Shop and Giant's Stairs Trail.

To see ratings, reviews, maps, and tourist information, you can read our Bailey Island trip itinerary planner.

Traveling by car from Phippsburg to Bailey Island takes an hour. In June, plan for daily highs up to 73°F, and evening lows to 54°F. On the 29th (Sat), you'll travel back home.
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Trails · Outdoors · Parks · Shopping

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.
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