24 days in New England Itinerary

24 days in New England Itinerary

Created using Inspirock New England itinerary maker

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Plan created by another user.Make it yours

Route & dates

1
Bennington
— 2 nights
2
Stowe
— 3 nights
3
North Conway
— 3 nights
4
New London
— 2 nights
5
Nantucket
— 3 nights
6
Oak Bluffs, Martha's Vineyard
— 2 nights
7
Rockland
— 2 nights
8
Bar Harbor, Mount Desert Island
— 3 nights
9
Portland
— 3 nights

2
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. You'll explore the less-touristy side of things at Silk Road Covered Bridge and Molly Stark Trail. There's still lots to do: look for gifts at Bennington Potters and take in the views from Burt Henry Covered Bridge.

To see where to stay, ratings, reviews, and tourist information, go to the Bennington online trip planner.

Sanford to Bennington is an approximately 7-hour flight. You can also drive; or do a combination of train and bus. Traveling from Sanford in June, you will find days in Bennington are a bit cooler (°F), and nights are much colder (°F). On the 3rd (Wed), you'll have the morning to explore before heading off to Stowe.

Things to do in Bennington

Outdoors Scenic Drive Shopping
Highlights from your plan
Bennington Potters ©
Bennington Potters
Silk Road Covered Bridge ©
Silk Road Covered Bridge
Burt Henry Covered Bridge ©
Burt Henry Covered Bridge

3
nights
Stowe

Stowe ©
Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Eschew the tourist crowds and head to Sterling Falls Gorge and Laughing Moon Chocolates. There's lots more to do: head outdoors with Bingham Falls, delve into the lush surroundings at Wiessner Woods, sample the fine beverages at Green Mountain Distillers, and hike along Stowe Recreation Path.

To see photos, other places to visit, ratings, and tourist information, read Stowe itinerary maker site.

You can drive from Bennington to Stowe in 3.5 hours. Other options are to do a combination of car and train; or take a bus. In June, daytime highs in Stowe are °F, while nighttime lows are °F. Wrap up your sightseeing on the 6th (Sat) early enough to drive to North Conway.

Things to do in Stowe

Parks Outdoors Nature

Side Trip

Green Mountain Distillers
Highlights from your plan
Wiessner Woods ©
Wiessner Woods
Bingham Falls ©
Bingham Falls
Trapp Family Lodge Outdoor Center ©
Trapp Family Lodge Outdoor Center

3
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.
Eschew the tourist crowds and head to Cathedral Ledge and White Horse Ledge. There's still lots to do: stroll through Cranmore Mountain Resort, look for gifts at Bavarian Chocolate Haus, stroll around Schouler Park, and take a memorable drive along Kancamagus Highway.

To find other places to visit, ratings, and other tourist information, go to the North Conway road trip planner.

You can drive from Stowe to North Conway in 3 hours. Alternatively, you can take a bus. Expect somewhat warmer evenings in North Conway when traveling from Stowe in June, with lows around °F. Finish up your sightseeing early on the 9th (Tue) so you can travel to New London.

Things to do in North Conway

Parks Outdoors Nature
Highlights from your plan
Schouler Park ©
Schouler Park
Cathedral Ledge ©
Cathedral Ledge
Cranmore Mountain Resort ©
Cranmore Mountain Resort

2
nights
New London

New London ©
New London is a seaport city and a port of entry on the northeast coast of the United States. On the 10th (Wed), admire the majestic nature at Thames River Heritage Park, thencontemplate the long history of Fort Trumbull State Park, thentake a leisurely stroll along Ocean Beach Park, and finally visit a coastal fixture at New London Harbor Light. Get ready for a full day of sightseeing on the 11th (Thu): identify plant and animal life at Connecticut College Arboretum.

To find reviews, traveler tips, other places to visit, and more tourist information, read New London journey site.

Traveling by car from North Conway to New London takes 4.5 hours. Alternatively, you can do a combination of car and flight. Expect a daytime high around °F in June, and nighttime lows around °F. Wrap up your sightseeing by early afternoon on the 11th (Thu) to allow enough time to travel to Nantucket.

Things to do in New London

Parks Historic Sites Nature
Highlights from your plan
Thames River Heritage Park ©
Thames River Heritage Park
Fort Trumbull State Park ©
Fort Trumbull State Park
Ocean Beach Park ©
Ocean Beach Park

3
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Explore hidden gems such as Madaket Beach and Surfside Beach. And it doesn't end there: enjoy the sea views from Brant Point Lighthouse, don't miss a visit to Nantucket Preservation Trust, relax in the rural setting at Moors End Farm, and enjoy the sand and surf at Jetties Beach.

To find more things to do, maps, other places to visit, and more tourist information, use the Nantucket tour itinerary planner.

You can drive from New London to Nantucket in 4.5 hours. Traveling from New London in June, expect nights in Nantucket to be about the same, around °F, while days are a bit cooler, around °F. Cap off your sightseeing on the 14th (Sun) early enough to catch the ferry to Oak Bluffs.

Things to do in Nantucket

Outdoors Parks Beaches
Highlights from your plan
Jetties Beach ©
Jetties Beach
Madaket Beach ©
Madaket Beach
Brant Point Lighthouse ©
Brant Point Lighthouse

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 15th (Mon), head outdoors with My Brother Charters, thenenjoy the sand and surf at Oak Bluffs Town Beach, thenkick back and relax at Joseph Sylvia State Beach, and finally enjoy the sea views from Edgartown Lighthouse. Get ready for a full day of sightseeing on the 16th (Tue): kick back and relax at Menemsha Hills, thencontemplate the long history of Aquinnah Cliffs, and then take a stroll through Martha's Vineyard Camp meeting Association (MVCMA).

To find more things to do, ratings, maps, and other tourist information, use the Oak Bluffs trip planner.

Getting from Nantucket to Oak Bluffs by ferry takes about 2 hours. In June, daily temperatures in Oak Bluffs can reach °F, while at night they dip to °F. Finish your sightseeing early on the 16th (Tue) to allow enough time to travel to Rockland.

Things to do in Oak Bluffs

Outdoors Parks Beaches

Side Trips

Edgartown Lighthouse, Aquinnah Cliffs, Menemsha Hills
Highlights from your plan
Oak Bluffs Town Beach ©
Oak Bluffs Town Beach
Edgartown Lighthouse ©
Edgartown Lighthouse

2
nights
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Start off your visit on the 17th (Wed): take a memorable tour with Tours, thenstop by Fiore Artisan Olive Oils and Vinegars, thenstroll around Buoy Park, and finally go for a walk through Rockland Harbor Trail. On the 18th (Thu), you'll have a packed day of sightseeing: walk around Harbor Park, thenvisit a coastal fixture at Rockland Breakwater Light, and then walk around Snow Marine Park.

To find maps, photos, more things to do, and other tourist information, go to the Rockland trip itinerary planning app.

Getting from Oak Bluffs to Rockland by flight takes about 4.5 hours. Other options: drive; or do a combination of ferry and bus. Expect a bit cooler weather when traveling from Oak Bluffs in June: highs in Rockland hover around °F, while lows dip to °F. Cap off your sightseeing on the 18th (Thu) early enough to go by car to Bar Harbor.

Things to do in Rockland

Parks Outdoors Tours
Highlights from your plan
Harbor Park ©
Harbor Park
Boat Tours & Water Sports
Rockland Breakwater Light ©
Rockland Breakwater Light

3
nights
Bar Harbor, Mount Desert Island

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Discover out-of-the-way places like Bar Island Trails and Egg Rock Light. There's lots more to do: hike along Great Head Trail, make a trip to Land Bridge to Bar Island, take in nature's colorful creations at Asticou Terraces / Thuya Garden, and go for a walk through Compass Harbor Trail.

To find traveler tips, other places to visit, photos, and other tourist information, you can read our Bar Harbor day trip planner.

Traveling by car from Rockland to Bar Harbor takes 2.5 hours. Alternatively, you can take a bus. In June, daytime highs in Bar Harbor are °F, while nighttime lows are °F. Finish your sightseeing early on the 21st (Sun) so you can drive to Portland.

Things to do in Bar Harbor

Parks Outdoors Trails

Side Trips

Asticou Terraces / Thuya Garden, Great Head Trail
Highlights from your plan
Boat Tours & Water Sports
Bar Island Trails ©
Bar Island Trails
Great Head Trail ©
Great Head Trail

3
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.
Eschew the tourist crowds and head to Casco Bay and Shipyard Brewing Company. Next up on the itinerary: trek along Eastern Prom Trail, brush up on your knowledge of spirits at Maine Craft Distilling, stroll around Deering Oaks Park, and make a trip to Harbor Fish Market.

For reviews, ratings, more things to do, and other tourist information, use the Portland tour itinerary planner.

You can drive from Bar Harbor to Portland in 3.5 hours. Other options are to take a bus; or do a combination of flight and bus. June in Portland sees daily highs of °F and lows of °F at night. Finish up your sightseeing early on the 24th (Wed) so you can travel back home.

Things to do in Portland

Parks Outdoors Breweries & Distilleries
Highlights from your plan
Deering Oaks Park ©
Deering Oaks Park
Shipyard Brewing Company ©
Shipyard Brewing Company
Fort Gorges ©
Fort Gorges

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