New England Road Trip Starting in Cape Cod

Question

Traveling from VA to visit family in Cape Cod mid-late September. Plan to stay there 2.5 days to visit with day trips to Nantucket & Martha’s Vineyard. We’ll begin our roadtrip there. Tentative itinerary below. Is it too aggressive? Feel free to add must sees, must do’s, & anything to avoid.

Day 1 - VA to Cape Cod (11hr drive)

Day 2 - Nantucket

Day 3 - Martha's Vineyard

Day 4 - travel to Newport RI in AM (1.5hr drive) & explore. Cliff Walk

Day 5 - travel to North Conway/White Mtn NH in AM (4hr drive) & explore.

Day 6 - White Mtn (Kancamagus Hwy)

Day 7 - travel to Bar Harbor in AM (4.5hr drive) & explore. Stops in Ogunquit & Kennebunkport

Day 8 - Acadia NP, Cadillac Mtn

Day 9 - Acadia NP in AM & travel to Portland ME in PM (3hr drive)

Day 10 - Portland ME

Day 11 - travel home to VA @ 11.5 hrs

Thank you in advance for your time & assistance!

Answer

Your itinerary looks like a fun and packed adventure across New England, but it might be a little tight, especially with some of the long drives involved. However, if you're okay with driving a bit each day and enjoying scenic stops along the way, it should be a great trip! Here are a few thoughts and suggestions for your road trip:

Day 1 - VA to Cape Cod (11hr drive): This is a long drive, but it’s doable. Be sure to take breaks and maybe stop at some interesting spots along the way. You could consider a stop in Connecticut for lunch or a quick exploration—perhaps Mystic Seaport or New Haven for a stretch. Since you’re traveling from VA, you might want to plan a nice dinner in Cape Cod to break up the day.

Day 2 - Nantucket: Nantucket is a beautiful island, and while a day trip can be enjoyable, it is a bit rushed. You’ll need to catch a ferry, so be mindful of the ferry schedules. Once you arrive, you’ll want to focus on exploring the town, visiting the Whaling Museum, and checking out the iconic Brant Point Lighthouse. If you're into history, a visit to the Nantucket Lightship Basket Museum is also a unique stop. Consider renting bikes to get around more easily.

Day 3 - Martha's Vineyard: Similar to Nantucket, a day trip to Martha's Vineyard is doable, but it’s another busy day. The ferry ride itself can take up a good portion of the day, so focus on one or two towns instead of trying to cover the entire island. Oak Bluffs is known for its colorful cottages and lively atmosphere, while Edgartown offers charming streets and a nice coastal vibe. You might also want to check out the Flying Horses Carousel and Gay Head Lighthouse.

Day 4 - Travel to Newport, RI (1.5hr drive) & explore - Cliff Walk: Newport is a gem, and the Cliff Walk is definitely a must-do. The coastal views are stunning, and the walk is relatively easy. Newport also offers the famous Gilded Age mansions, like The Breakers, which you can tour if you're interested in history. After your walk, you can explore Thames Street for shopping or grab some fresh seafood at one of the many waterfront restaurants.

Day 5 - Travel to North Conway/White Mountains, NH (4hr drive) & explore: This drive is longer, but you’re heading into a beautiful area! If you’re into outdoor activities, North Conway is a great base for the White Mountains. You can explore Mount Washington or take a scenic drive through the area. If you’re not into hiking, a drive along the Kancamagus Highway is one of the most scenic routes in New England, especially in the fall. There are plenty of quaint shops and cafes in North Conway, perfect for exploring after your drive.

Day 6 - White Mountain (Kancamagus Highway): The Kancamagus Highway is amazing, especially if you're into nature and fall foliage (if your timing aligns). It's a 34-mile stretch through the White Mountains that offers breathtaking views. Consider stopping at some of the scenic pull-offs for photos and short walks. If you're up for a little hike, the Sabbaday Falls or the Rocky Gorge are both beautiful and easily accessible from the highway.

Day 7 - Travel to Bar Harbor, ME (4.5hr drive) & explore - Stops in Ogunquit & Kennebunkport: Bar Harbor is worth the drive, but it’s another long one. If you're stopping in Ogunquit and Kennebunkport, you could explore the Marginal Way in Ogunquit—a beautiful coastal walk—and Kennebunkport offers lovely shops and the chance to see the famous Bush family estate. Once in Bar Harbor, be sure to explore the town and get a feel for its charm. You could also check out the Abbe Museum or take a boat tour for scenic views.

Day 8 - Acadia National Park, Cadillac Mountain: Acadia National Park is amazing, and Cadillac Mountain is a must-see, especially if you’re up for an early morning to catch the sunrise. There are plenty of scenic drives, and you can visit Jordan Pond and the Thunder Hole to see the crashing waves. If you have time, consider a visit to the Schoodic Peninsula for a quieter, less crowded experience.

Day 9 - Acadia National Park in the AM & Travel to Portland, ME in PM (3hr drive): If you're short on time, you may want to focus on a few of Acadia's key spots in the morning, like the Cadillac Summit, the Seawall, or the Bass Harbor Head Lighthouse. Afterward, head south to Portland. Portland is a cool city, known for its food scene (especially seafood), the Old Port district, and lighthouses. It’s worth the stop for a more urban vibe after being in more rural areas.

Day 10 - Portland, ME: Portland has a lot to offer. Consider visiting the Portland Head Light, one of the most iconic lighthouses in Maine, or check out the Eastern Promenade for waterfront views. Portland’s Old Port is full of boutiques, cafes, and seafood restaurants, like the popular Eventide Oyster Co. If you enjoy art, visit the Portland Museum of Art.

Day 11 - Travel home to VA (11.5hr drive): This will be a long drive, so make sure you plan for rest stops, food breaks, and maybe a stretch in a scenic town along the way. If you need a good pit stop, consider the charming town of Woodstock, VA, for a break and a bite to eat.

Final Thoughts: Your itinerary is doable, but it's a bit packed with long drives. If you're okay with the driving and want to explore as much as possible, go for it! But if you’re looking to relax a bit more, you may want to consider trimming down the number of destinations or adjusting some of the driving times. You could also add some more time to enjoy Portland or Bar Harbor. Either way, this will be a wonderful trip!

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