23 days in New England Itinerary

23 days in New England Itinerary

Created using Inspirock New England trip itinerary maker

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Route & dates

23 days in New England Itinerary

Start: Newark
Fly + Drive:  5​h 30​min
1
Lincoln
— 3 nights
Drive:  1​h 15​min
2
North Conway
— 2 nights
Drive:  1​h 45​min
3
Portland
— 4 nights
Drive:  3​h 30​min
4
Bar Harbor, Mount Desert Island
— 5 nights
Fly:  5​h 30​min
5
Nantucket
— 3 nights
Drive:  2​h 30​min
6
Oak Bluffs, Martha's Vineyard
— 2 nights
Drive:  2​h 15​min
7
Eastham
— 3 nights
Drive + Fly:  5​h 15​min
End: Newark

3
nights
Lincoln

Lincoln ©
Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Family-friendly places like Lost River Gorge and Boulder Caves and Ice Castles will thrill your kids. You'll explore the less-touristy side of things at Franconia Notch State Park and Riverwalk Covered Bridge. Step out of Lincoln with an excursion to Wallace Horse Cemetery in Littleton--about 42 minutes away. There's still lots to do: make a splash at Whales Tale Waterpark, take in the dramatic natural features at The Basin at Franconia Notch State Park, stop by Chutters, and kick your exploration up a notch at some of the top local zipline courses and adventure parks.

To find photos, traveler tips, more things to do, and more tourist information, use the Lincoln holiday site .

Newark to Lincoln is an approximately 5.5-hour combination of flight and car. You can also drive. Prepare for little chillier weather when traveling from Newark in August: high temperatures in Lincoln hover around 78°F and lows are around 54°F. Wrap up your sightseeing on the 8th (Thu) early enough to drive to North Conway.

Things to do in Lincoln

Parks Theme Parks Nature

Side Trips

Littleton, Franconia, Lost River Gorge and Boulder Caves
Highlights from your plan
Lost River Gorge and Boulder Caves ©
Whales Tale Waterpark ©
Whales Tale Waterpark
Ice Castles ©
Ice Castles

2
nights
North Conway

North Conway ©
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Kick off your visit on the 9th (Fri): see the sky in a new way at Mount Washington Observatory Weather Discovery Center, then explore the striking landscape at Cathedral Ledge, and then admire the striking features of Castle in the Clouds. Get ready for a full day of sightseeing on the next day: admire the sheer force of Glen Ellis Falls and then stroll through Cranmore Mountain Resort.

To see reviews, more things to do, other places to visit, and tourist information, you can read our North Conway itinerary maker app .

You can drive from Lincoln to North Conway in 1.5 hours. Alternatively, you can take a bus. In August, daily temperatures in North Conway can reach 75°F, while at night they dip to 59°F. Finish your sightseeing early on the 10th (Sat) to allow enough time to drive to Portland.

Things to do in North Conway

Parks Outdoors Nature

Side Trips

Castle in the Clouds, Glen Ellis Falls
Highlights from your plan
Cathedral Ledge ©
Cathedral Ledge
Cranmore Mountain Resort ©
Cranmore Mountain Resort

4
nights
Portland

Portland ©
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.
Bring the kids along to Long Sands Beach and Wells Beach. Explore the numerous day-trip ideas around Portland: Maine Maritime Museum (in Bath), Pemaquid Point Lighthouse (in Bristol) and Rockland (Rockland Breakwater Light & Farnsworth Art Museum). There's more to do: get in on the family fun at Canobie Lake Park.

To find traveler tips, reviews, maps, and other tourist information, read Portland online attractions planner .

Traveling by car from North Conway to Portland takes 2 hours. Alternatively, you can do a combination of taxi and bus. In August, daily temperatures in Portland can reach 79°F, while at night they dip to 59°F. Wrap up your sightseeing on the 14th (Wed) to allow time to drive to Bar Harbor.

Things to do in Portland

Beaches Outdoors Historic Sites

Side Trips

Rockland, Maine Maritime Museum, Canobie Lake Park, Pemaquid Point Lighthouse, Long Sands Beach
Highlights from your plan
Wells Beach ©
Wells Beach
Canobie Lake Park ©
Canobie Lake Park
Long Sands Beach ©
Long Sands Beach

5
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Step off the beaten path and head to Champlain Mountain & Beehive Loop Trail and Gorham Mountain Trail. You'll visit kid-friendly attractions like Pirate's Cove Miniature Golf and Sand Beach. Explore Bar Harbor's surroundings by going to Bass Harbor Head Lighthouse (in Bass Harbor) and Schoodic Point (in Winter Harbor). Next up on the itinerary: explore the landscape on two wheels at Carriage Roads, get interesting insight from Tours, look for gifts at Christmas Spirit Shop, and take in the dramatic natural features at Schoodic Peninsula.

To see maps, more things to do, and tourist information, you can read our Bar Harbor trip planner .

You can drive from Portland to Bar Harbor in 3.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. In August, plan for daily highs up to 75°F, and evening lows to 57°F. Finish up your sightseeing early on the 19th (Mon) so you can travel to Nantucket.

Things to do in Bar Harbor

Outdoors Parks Trails

Side Trips

Acadia National Park, Bass Harbor Head Lighthouse, Somesville Historical Museum and Gardens, Schoodic Point
Highlights from your plan
Sand Beach ©
Sand Beach
Champlain Mountain & Beehive Loop Trail ©
Kayaking & Canoeing

3
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kids will enjoy Madaket Beach and Jetties Beach. Discover out-of-the-way places like Sankaty Head Lighthouse and Brant Point Lighthouse. The adventure continues: tour the pleasant surroundings at Surfside Beach, sample the tasty concoctions at Cisco Brewers, stop by The Hub, and enjoy the sand and surf at Cisco Beach.

To find more things to do, photos, reviews, and tourist information, read our Nantucket online day trip planner .

Traveling by flight from Bar Harbor to Nantucket takes 5.5 hours. Alternatively, you can do a combination of car and flight; or do a combination of car and ferry. Plan for somewhat warmer nights when traveling from Bar Harbor in August since evenings lows in Nantucket dip to 63°F. Wrap up your sightseeing on the 22nd (Thu) to allow time to drive to Oak Bluffs.

Things to do in Nantucket

Beaches Outdoors Parks
Highlights from your plan
Madaket Beach ©
Madaket Beach
Cisco Beach ©
Cisco Beach
Jetties Beach ©
Jetties Beach

2
nights
Oak Bluffs, Martha's Vineyard

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. On the 23rd (Fri), enjoy the sand and surf at Menemsha Public Beach, then stroll around Ocean Park, and then don't miss a visit to Flying Horses Carousel. Get ready for a full day of sightseeing on the next day: stop by Alley's General Store, then enjoy the sea views from Gay Head Lighthouse, then relax in the rural setting at Island Alpaca Company of Martha's Vineyard, and finally wander the streets of Martha's Vineyard Camp meeting Association (MVCMA).

To see maps, more things to do, where to stay, and more tourist information, you can read our Oak Bluffs road trip site .

Traveling by car from Nantucket to Oak Bluffs takes 2.5 hours. In August, daytime highs in Oak Bluffs are 79°F, while nighttime lows are 59°F. Finish up your sightseeing early on the 24th (Sat) so you can go by car to Eastham.

Things to do in Oak Bluffs

Parks Beaches Outdoors

Side Trips

Alley's General Store, Menemsha Public Beach, Gay Head Lighthouse
Highlights from your plan
Menemsha Public Beach ©
Menemsha Public Beach
Flying Horses Carousel ©
Flying Horses Carousel

3
nights
Eastham

Eastham ©
Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. You'll visit kid-friendly attractions like Cape Cod National Seashore and Nauset Beach. Eschew the tourist crowds and head to Coast Guard Beach and Marconi Beach. Explore Eastham's surroundings by going to Provincetown (Provincetown Library & Herring Cove Beach). It doesn't end there: look for gifts at Gustare Oils and Vinegars.

For traveler tips, reviews, other places to visit, and tourist information, read Eastham trip planner .

Traveling by car from Oak Bluffs to Eastham takes 2.5 hours. Expect a daytime high around 78°F in August, and nighttime lows around 63°F. Finish your sightseeing early on the 27th (Tue) so you can travel back home.

Things to do in Eastham

Beaches Outdoors Parks

Side Trips

Provincetown, Cape Cod National Seashore, Gustare Oils and Vinegars, Marconi Beach, Nauset Beach
Highlights from your plan
Herring Cove Beach ©
Herring Cove Beach
Cape Cod National Seashore ©
Cape Cod National Seashore
Nauset Beach ©
Nauset Beach

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