36 days in Maine Itinerary

36 days in Maine Itinerary

Created using Inspirock United States holiday maker

©
Plan created by another user. Make it yours
1
South Portland
— 2 nights
2
Portland
— 3 nights
3
Kennebunkport
— 2 nights
4
Wells
— 2 nights
5
Ogunquit
— 2 nights
6
Boothbay Harbor
— 2 nights
7
Greenville
— 1 night
8
Millinocket
— 1 night
9
Bangor
— 3 nights
10
Camden
— 2 nights
11
Rockland
— 2 nights
12
Deer Isle
— 2 nights
13
Southwest Harbor
— 2 nights
14
Bass Harbor
— 1 night
15
Mount Desert
— 2 nights
16
Acadia National Park
— 2 nights
17
Bar Harbor
— 3 nights

S M T W T F S
30
31
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25
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29
30
1
2
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10

2
nights
South Portland

South Portland ©
South Portland is a city in Cumberland County, Maine, United States, and is the fourth-largest city in the state, incorporated in 1898. Get ready for a full day of sightseeing on the 6th (Sun): steep yourself in history at Goddard Mansion, take a tour by water with Salt and Mist Sea Tours, then get some jogging in at Greenbelt Walkway, then brush up on your military savvy at Maine Military Museum, and finally look for all kinds of wild species at Mill Creek Park.

To find where to stay, photos, traveler tips, and more tourist information, go to the South Portland trip itinerary planning website.

Chicago to South Portland is an approximately 5-hour combination of flight and car. You can also drive. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Prepare for little chillier weather when traveling from Chicago in September: high temperatures in South Portland hover around 73°F and lows are around 52°F. On the 7th (Mon), wrap the sightseeing up by early afternoon so you can drive to Portland.

Things to do in South Portland

Outdoors · Historic Sites · Museums · Parks

Side Trip

Find places to stay Sep 5 — 7:
Highlights from your plan
Spring Point Shoreway ©
Spring Point Shoreway
Goddard Mansion ©
Goddard Mansion
Fort Preble ©
Fort Preble

3
nights
Portland

Portland ©

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.
Start off your visit on the 7th (Mon): admire the majestic nature at Mackworth Island. Keep things going the next day: explore the different monuments and memorials at Eastern Cemetery, examine the collection at Maine Jewish Museum, do a tasting at Maine Mead Works, see the interesting displays at 5th Maine Museum, then see the interesting displays at Umbrella Cover Museum, and finally explore the landscape on two wheels at Eastern Promenade Trail.

To find more things to do, maps, where to stay, and other tourist information, read Portland trip planner.

Portland is very close to South Portland. Expect a daytime high around 73°F in September, and nighttime lows around 52°F. Finish your sightseeing early on the 10th (Thu) to allow enough time to drive to Kennebunkport.

Things to do in Portland

Historic Sites · Museums · Outdoors · Parks

Side Trip

Find places to stay Sep 7 — 10:
Highlights from your plan
Maine Jewish Museum ©
Maine Jewish Museum
Eastern Promenade Trail ©
Eastern Promenade Trail
Wadsworth-Longfellow House ©
Wadsworth-Longfellow House

2
nights
Kennebunkport

Kennebunkport ©
Kennebunkport is a town in York County, Maine, United States. Kick off your visit on the 10th (Thu): race across the water with New England EcoAdventures, take in the exciting artwork at Maine Art Hill, indulge in some personalized pampering at Cottage Breeze Day Spa & Boutique, stop by Maine-ly Drizzle, then view the masterpieces at W. Robert Paine Gallery, and finally view the masterpieces at Compliments. On the 11th (Fri), you'll have a packed day of sightseeing: take in the exciting artwork at Mast Cove Gallery, learn about all things military at First Families Kennebunkport Museum, then admire the masterpieces at The Brick Store Museum, then enjoy the sand and surf at Parsons Beach, and finally enjoy the sand and surf at Mother's Beach.

To find ratings, more things to do, traveler tips, and other tourist information, use the Kennebunkport route planner.

You can drive from Portland to Kennebunkport in an hour. Alternatively, you can take a bus; or do a combination of train and bus. Expect a daytime high around 74°F in September, and nighttime lows around 48°F. Wrap up your sightseeing on the 12th (Sat) early enough to drive to Wells.

Things to do in Kennebunkport

Museums · Shopping · Outdoors · Parks

Side Trip

Find places to stay Sep 10 — 12:
Highlights from your plan
Maine Art Hill ©
Maine Art Hill
First Families Kennebunkport Museum ©
First Families Kennebunkport Museum
Parsons Beach ©
Parsons Beach

2
nights
Wells

Wells ©
Wells is a town in York County, Maine, United States. Kick off your visit on the 12th (Sat): look for gifts at Wallingford Farm, relax in the rural setting at Spiller Farm, then experience rural life at Chase Farms, and finally kick back and relax at Moody Beach. Get ready for a full day of sightseeing on the next day: delve into the lush surroundings at McDougal Orchards, take an in-depth tour of New Hampshire Farm Museum, contemplate the waterfront views at Pine River Pond, then get engrossed in the history at 19th Century Willowbrook Village, and finally indulge your thirst for a good beer at Hidden Cove Brewing Company.

To find more things to do, where to stay, other places to visit, and tourist information, use the Wells trip itinerary planning site.

Wells is just a short distance from Kennebunkport. In September, daily temperatures in Wells can reach 74°F, while at night they dip to 48°F. Cap off your sightseeing on the 14th (Mon) early enough to go by car to Ogunquit.

Things to do in Wells

Parks · Outdoors · Beaches · Museums

Side Trips

Find places to stay Sep 12 — 14:
Highlights from your plan
Moody Beach ©
Moody Beach
New Hampshire Farm Museum ©
New Hampshire Farm Museum
19th Century Willowbrook Village ©
19th Century Willowbrook Village

2
nights
Ogunquit

Ogunquit ©
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
On the 14th (Mon), stroll the grounds of St. John's Episcopal Church, admire the natural beauty at Moffatt-Ladd House & Garden, contemplate the long history of John Paul Jones House, part of the Portsmouth Historical Society, contemplate the long history of Warner House, then contemplate the long history of Wentworth-Gardner House, and finally appreciate the history behind African Burying Ground. Keep things going the next day: get outside with Fisherman's Walk, get advice or help at Ogunquit Memorial Library, view the masterpieces at PANACHE FINE JEWELRY AND ART GALLERY, then take an in-depth tour of Ogunquit Heritage Museum, then enjoy the sea views from Portsmouth Harbor Lighthouse, and finally get to know the fascinating history of Harbour Place Marina.

To see other places to visit, traveler tips, where to stay, and tourist information, read our Ogunquit route maker website.

Ogunquit is just a short distance from Wells. In September, plan for daily highs up to 74°F, and evening lows to 48°F. Cap off your sightseeing on the 16th (Wed) early enough to go by car to Boothbay Harbor.

Things to do in Ogunquit

Historic Sites · Museums · Parks · Outdoors

Side Trips

Find places to stay Sep 14 — 16:
Highlights from your plan
Ogunquit Memorial Library ©
Ogunquit Memorial Library
Portsmouth Harbor Lighthouse ©
Portsmouth Harbor Lighthouse

2
nights
Boothbay Harbor

Boothbay Harbor ©
Boothbay Harbor is a town in Lincoln County, Maine, United States. Kick off your visit on the 16th (Wed): trek along Porters Preserve, tour the pleasant surroundings at Seguin Island and Lighthouse, visit a coastal fixture at Doubling Point Lighthouse, stroll around South End Dog Park, then take an in-depth tour of Maine Heritage Village, and finally look for all kinds of wild species at Ovens Mouth Preserves. Get ready for a full day of sightseeing on the next day: take in the architecture and atmosphere at The Wilson Memorial Chapel, stop by Dirty Bird Pottery, view the masterpieces at Abacus Gallery, take an in-depth tour of Boothbay Region Historical Society Museum, then take a stroll around Opera House at Boothbay Harbor, and finally take a memorable tour with Hay-Val Charters.

For where to stay, other places to visit, reviews, and other tourist information, go to the Boothbay Harbor trip itinerary planner.

Getting from Ogunquit to Boothbay Harbor by car takes about 2 hours. Other options: do a combination of taxi and train; or do a combination of bus and taxi. In September, daytime highs in Boothbay Harbor are 73°F, while nighttime lows are 51°F. Finish your sightseeing early on the 18th (Fri) so you can travel to Greenville.

Things to do in Boothbay Harbor

Parks · Outdoors · Museums · Historic Sites

Side Trips

Find places to stay Sep 16 — 18:
Highlights from your plan
Porters Preserve ©
Porters Preserve
The Wilson Memorial Chapel ©
The Wilson Memorial Chapel
Doubling Point Lighthouse ©
Doubling Point Lighthouse

1
night
Greenville

Greenville ©
Greenville is a town in Piscataquis County, Maine, United States. On the 18th (Fri), immerse yourself in nature at Mount Kineo State Park, then surround yourself with nature on Lone Wolf Guiding Services, then get engrossed in the history at Moosehead Historical Society, and finally contemplate the waterfront views at Prong Pond.

Plan my trip to Greenville with suggested itineraries provided by Inspirock.

You can drive from Boothbay Harbor to Greenville in 3 hours. Another option is to drive. When traveling from Boothbay Harbor in September, plan for little chillier days in Greenville, with highs around 68°F, while nights are about the same with lows around 50°F. Wrap up your sightseeing on the 19th (Sat) to allow time to drive to Millinocket.

Things to do in Greenville

Wildlife · Parks · Nature · Outdoors

Side Trip

Find places to stay Sep 18 — 19:
Highlights from your plan
Mount Kineo State Park ©
Mount Kineo State Park
Moosehead Historical Society ©
Moosehead Historical Society
Prong Pond ©
Prong Pond

1
night
Millinocket

Millinocket ©
Millinocket is a town in Penobscot County, Maine, United States.The population was 4,506 at the 2010 census. On the 19th (Sat), view the masterpieces at Moose Prints Gallery and Gifts, surround yourself with nature on Mainely Photos Moose & Photo Tours, and then take a tour by water with Jump and Raft. Keep things going the next day: look for all kinds of wild species at Katahdin Woods and Waters National Monument, then get engrossed in the history at Lumberman's Museum, and then explore the activities along Jerry Pond.

To find photos, traveler tips, other places to visit, and other tourist information, use the Millinocket day trip planner.

You can drive from Greenville to Millinocket in 2 hours. September in Millinocket sees daily highs of 72°F and lows of 50°F at night. Finish your sightseeing early on the 20th (Sun) so you can drive to Bangor.

Things to do in Millinocket

Outdoors · Tours · Wildlife · Parks

Side Trip

Find places to stay Sep 19 — 20:
Highlights from your plan
Jump and Raft ©
Jump and Raft
Katahdin Woods and Waters National Monument ©
Lumberman's Museum ©
Lumberman's Museum

3
nights
Bangor

Bangor ©
Bangor is a city along the Penobscot River in the U.S. Kick off your visit on the 21st (Mon): take an in-depth tour of Maine Forest and Logging Museum, examine the collection at Page Farm and Home Museum, then take a tour by water with Tracewski Fishing Adventures, and finally explore the activities along Craig's Pond. Here are some ideas for day two: stroll the grounds of Buck Cemetery, get engrossed in the history at Bucksport Historical Society, do a tasting at Winterport Winery, then brush up on your military savvy at Bangor Historical Society and Thomas A. Hill House Museum, then sample the tasty concoctions at 2 Feet Brewing, and finally hike along Kenduskeag Stream Heritage Trail.

Make your Bangor itinerary with Inspirock to find out what to see and where to go.

You can drive from Millinocket to Bangor in 1.5 hours. September in Bangor sees daily highs of 73°F and lows of 51°F at night. Cap off your sightseeing on the 23rd (Wed) early enough to go by car to Camden.

Things to do in Bangor

Museums · Outdoors · Tours · Parks

Side Trips

Find places to stay Sep 20 — 23:
Highlights from your plan
Maine Forest and Logging Museum ©
Maine Forest and Logging Museum
Bucksport Historical Society ©
Bucksport Historical Society
Winterport Winery ©
Winterport Winery

2
nights
Camden

Camden ©
On the 23rd (Wed), take in the spiritual surroundings of Chestnut Street Baptist Church, then don't miss a visit to Vesper Hill Children's Chapel, then look for all kinds of wild species at Fernald's Neck Preserve, and finally add some adventure to your tour with Ducktrap Kayaking. Keep things going the next day: look for all kinds of wild species at Hope Elephants, explore the landscape on two wheels at Passy Rail Trail, get engrossed in the history at Belfast Historical Society & Museum, look for gifts at French & Brawn Market Place, then take in the exciting artwork at Ducktrap Bay Trading Co, and finally do a tasting at Sweetgrass Farm Winery and Distillery.

To see other places to visit, more things to do, where to stay, and more tourist information, read our Camden trip itinerary planning app.

Getting from Bangor to Camden by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around 69°F in September, and nighttime lows around 51°F. Cap off your sightseeing on the 25th (Fri) early enough to go by car to Rockland.

Things to do in Camden

Parks · Wildlife · Outdoors · Tours

Side Trips

Find places to stay Sep 23 — 25:
Highlights from your plan
Fernald's Neck Preserve ©
Fernald's Neck Preserve
Beech Hill Reserve ©
Beech Hill Reserve
Sweetgrass Farm Winery and Distillery ©
Sweetgrass Farm Winery and Distillery

2
nights
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Kick off your visit on the 25th (Fri): see what you can catch with Morning In Maine Boat Tour, get engrossed in the history at General Henry Knox Museum / Montpelier, explore the world behind art at Olson House, then have fun and explore at Coastal Children's Museum, and finally admire the majestic nature at Owl's Head State Park. Get ready for a full day of sightseeing on the next day: play a few rounds at Samoset Resort Golf Course, admire the masterpieces at Center for Maine Contemporary Art (CMCA), then examine the collection at Sail Power and Steam Museum, then do a tasting at Breakwater Vineyards, and finally immerse yourself in nature at Birch Point Beach State Park.

For reviews, more things to do, ratings, and more tourist information, read Rockland day trip website.

Rockland is very close to Camden. September in Rockland sees daily highs of 69°F and lows of 51°F at night. Finish up your sightseeing early on the 27th (Sun) so you can travel to Deer Isle.

Things to do in Rockland

Museums · Outdoors · Parks · Nature

Side Trips

Find places to stay Sep 25 — 27:
Highlights from your plan
Sail Power and Steam Museum ©
Sail Power and Steam Museum
Olson House ©
Olson House
Samoset Resort Golf Course ©
Samoset Resort Golf Course

2
nights
Deer Isle

Deer Isle ©
Deer Isle is a town in Hancock County, Maine, United States. Kick off your visit on the 27th (Sun): take a stroll through Stonington Village, admire the majestic nature at Fort George State Park, then admire the majestic nature at Fort Madison State Park, and finally look for gifts at Blue Hill Co-op Community Market. Get ready for a full day of sightseeing on the next day: stroll through Edgar M. Tennis Preserve, walk around Settlement Quarry Preserve, then look for all kinds of wild species at Barred Island Preserve, then see the interesting displays at Deer Isle-Stonington Historical Society, and finally make a trip to Deer Isle Village.

Discover how to plan a Deer Isle trip in just a few steps with Inspirock's itinerary builder.

Travel from Rockland to Deer Isle in 2 hours. In September in Deer Isle, expect temperatures between 70°F during the day and 52°F at night. Finish up your sightseeing early on the 29th (Tue) so you can travel to Southwest Harbor.

Things to do in Deer Isle

Parks · Nature · Neighborhoods · Outdoors

Side Trips

Find places to stay Sep 27 — 29:
Highlights from your plan
Stonington Village ©
Stonington Village
Barred Island Preserve ©
Barred Island Preserve
Deer Isle-Stonington Historical Society ©
Deer Isle-Stonington Historical Society

2
nights
Southwest Harbor

Southwest Harbor ©
Southwest Harbor is a town in Hancock County, Maine, United States. On the 29th (Tue), hike along Perpendicular Trail, admire the natural beauty at Abby Aldrich Rockefeller Garden, hike along Beech Cliff Loop, then identify plant and animal life at Pretty Marsh Picnic Area, and finally take in the awesome beauty at Mansell Mountain. Get ready for a full day of sightseeing on the next day: stop by Manset Little Farm, then trek along Wonderland Trail, and then hit the best photo ops around with J.K. Putnam Photography.

For more things to do, where to stay, other places to visit, and other tourist information, read our Southwest Harbor trip planner.

Traveling by journey from Deer Isle to Southwest Harbor takes 1.5 hours. September in Southwest Harbor sees daily highs of 70°F and lows of 52°F at night. Finish your sightseeing early on the 1st (Thu) so you can drive to Bass Harbor.

Things to do in Southwest Harbor

Parks · Outdoors · Trails · Tours

Side Trips

Find places to stay Sep 29 — Oct 1:
Highlights from your plan
Wonderland Trail ©
Wonderland Trail
Perpendicular Trail ©
Perpendicular Trail
Beech Cliff Loop ©
Beech Cliff Loop

1
night
Bass Harbor

Bass Harbor ©
On the 1st (Thu), take a tour by water with Island Cruises, then visit a coastal fixture at Bass Harbor Head Lighthouse, then examine the collection at The Seal Cove Auto Museum, and finally appreciate the extensive heritage of Ship Harbor Nature Trail. On the next day, head off the coast to Swans Island.

To find more things to do, reviews, where to stay, and other tourist information, read Bass Harbor online travel route builder.

Bass Harbor is just a short distance from Southwest Harbor. In October, daily temperatures in Bass Harbor can reach 59°F, while at night they dip to 42°F. You'll have a few hours on the 2nd (Fri) to wrap things up before traveling to Mount Desert.

Things to do in Bass Harbor

Historic Sites · Outdoors · Tours · Museums

Side Trip

Find places to stay Oct 1 — 2:
Highlights from your plan
Island Cruises ©
Island Cruises
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum
Ship Harbor Nature Trail ©
Ship Harbor Nature Trail

2
nights
Mount Desert

Mount Desert ©
Mount Desert is a town on Mount Desert Island in Hancock County, Maine, United States. Start off your visit on the 3rd (Sat): examine the collection at Maine Granite Industry Museum, then explore the striking landscape at Somes Sound, then take in nature's colorful creations at Asticou Terraces / Thuya Garden, and finally don't miss a visit to Harbourside Drive. Get ready for a full day of sightseeing on the next day: take in the awesome beauty at Penobscot Mountain, admire the natural beauty at Asticou Azalea Garden, and then learn about wildlife with up-close encounters at Kisma Preserve.

To find where to stay, maps, more things to do, and tourist information, you can read our Mount Desert trip itinerary builder tool.

Mount Desert is very close to Bass Harbor. Expect a daytime high around 59°F in October, and nighttime lows around 42°F. On the 4th (Sun), wrap the sightseeing up by early afternoon so you can drive to Acadia National Park.

Things to do in Mount Desert

Parks · Nature · Zoos & Aquariums · Museums

Side Trip

Find places to stay Oct 2 — 4:
Highlights from your plan
Asticou Azalea Garden ©
Asticou Azalea Garden
Asticou Terraces / Thuya Garden ©
Asticou Terraces / Thuya Garden
Penobscot Mountain ©
Penobscot Mountain

2
nights
Acadia National Park

Acadia National Park ©

First Eastern National Park

The first national park east of the Mississippi River, Acadia National Park draws visitors with its rugged landscape of ocean shoreline, low-slung granite mountains, dense woodlands, and pristine lakes.
On the 5th (Mon), head outdoors with Dorr Mountain, go for a charming ride with Carriages of Acadia, take your sightseeing to a higher altitude at Day Mountain, then take an in-depth tour of Somesville Historical Museum and Gardens, and finally look for all kinds of wild species at Indian Point Blagden Preserve. Keep things going the next day: take in the natural beauty of Sieur de Monts Spring, then hike along The Bowl Trail, and then trek along Heart of Acadia Loop.

To find where to stay, other places to visit, more things to do, and tourist information, use the Acadia National Park trip itinerary app.

Acadia National Park is very close to Mount Desert. In October, daytime highs in Acadia National Park are 59°F, while nighttime lows are 42°F. Wrap up your sightseeing on the 6th (Tue) to allow time to drive to Bar Harbor.

Things to do in Acadia National Park

Parks · Outdoors · Trails · Nature

Side Trip

Find places to stay Oct 4 — 6:
Highlights from your plan
Carriages of Acadia ©
Carriages of Acadia
Heart of Acadia Loop ©
Heart of Acadia Loop
Sieur de Monts Spring ©
Sieur de Monts Spring

3
nights
Bar Harbor

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Let the collections at Little Village Gifts and Whopaints Gallery capture your imagination. Get some historical perspective at St. Saviour's Church : and Egg Rock Light. Explore Bar Harbor's surroundings by going to Aquaterra Adventures (in Sullivan), Catherine Hill Winery (in Cherryfield) and Bartlett Maine Estate Winery (in Gouldsboro). The adventure continues: explore the wealth of natural beauty at Eagle Lake Acadia National Park, gain interesting insight with Bar Harbor Ghost Tours, take a memorable tour with Wild Iris Farm, and trek along Cadillac Mountain North Ridge Trail.

To see maps, reviews, other places to visit, and tourist information, go to the Bar Harbor online attractions planner.

Bar Harbor is just a short distance from Acadia National Park. In October, daytime highs in Bar Harbor are 59°F, while nighttime lows are 42°F. Finish your sightseeing early on the 9th (Fri) so you can travel back home.

Things to do in Bar Harbor

Outdoors · Tours · Parks · Museums

Side Trips

Find places to stay Oct 6 — 9:
Highlights from your plan
Cadillac Mountain North Ridge Trail ©
Cadillac Mountain North Ridge Trail
Eagle Lake Acadia National Park ©
Eagle Lake Acadia National Park
Egg Rock Light ©
Egg Rock Light

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