10 Days on Cape Cod this September

Old Mar 11th, 2023, 03:28 PM
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10 Days on Cape Cod this September

Hello all!

My husband and I are planning a trip out to Cape Cod at the end of September (20 - 30th). We'll be visiting distant relatives, some of whom I'll be meeting for the first time and are looking to explore the area on our own while we're there as well. We'll be flying into Boston and renting a car, and would love some guidance on the best way to break up our time on the Cape.

We have lodging set for Days 1-5 and are feeling good about our plan for that portion of our trip, but we're having trouble figuring out how to break up Days 6-9/10. I know that the drive from Falmouth to Provincetown isn't long if driven in a straight shot, but we'd like to stop along the way - visiting shops and views as we go.

Day 1: Arrive in Boston / Overnight in Hopkinton visiting family

Day 2: Travel to Sandwich / Exploring Sandwich and visiting family.

Day 3: Exploring Sandwich and visiting family.

Day 4: Early Wood's Hole ferry to Martha's Vineyard. Stay near Oak Bluffs at an AirBnB (already booked!)

Day 5: Explore Martha's Vineyard. Stay near Oak Bluffs at an AirBnB (already booked!)
While we're on MV -- Chappaquiddick, Mytoi, Edgartown, Oak Bluffs, gingerbread cottages, Aquinnah/Gay Head Cliffs

Day 6 - 9: Explore the Cape from Falmouth to Provincetown

Day 9 or 10: Head back to Boston

Day 11: Fly home

This time of year, is it best to book every night in advance, or would it be possible to play it by ear with lodging? Ideally we wouldn't be moving hotels every night, but can see that it might make sense to spend an evening in Falmouth, a day in Chatham, and a couple days in Provincetown.

For reference, we're in our 40s -- considered going to Nantucket, but Provincetown sounded a little more our style. We'd like to spend time in charming downtowns, ride bikes, hike, eat great local food, go antiquing (esp on Route 6A), go to the seashore for the views- maybe a picnic, visit lighthouses, visit a winery or brewery, and potentially get on the water via a sail, kayak, or whale watching tour.

Would love any recos on what towns best fit what we're looking for and how to split that time -- Thanks so much!
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Old Mar 11th, 2023, 08:31 PM
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For whale watching, look at Barnstable and Provincetown.
You give three days , 6-9, to explore all the way out to Provincetown.
By bodies of water and a nice town to visit:
Nantucket Sound- Harwichport .
You can drive by the Kennedy Compound in Hyannisport.
Cape Cod Bay: Brewster
Atlantic Ocean- starts in beautiful Chatham and goes out to Provincetown. Orleans is at the elbow and has both the Atlantic Ocean ,beautiful Nauset Beach, and Cape Cod Bay.Stay in Chatham, maybe Brewster. On the way out to Provincetown you can stay in Wellfleet or Truro.
Cape Cod is large! I tried to narrow down areas by body of water. There are also 365 fresh water lakes and ponds on the Cape.
Honestly Provincetown is interesting but it wouldn’t be my recommendation other than to day trip. Luckily, you will be on the Cape off season so crowds will be much less.
President Kennedy created the Cape Cod National Seashore which has protected the Atlantic shores of the Cape from development. There is a National Seashore Visitor Center in Eastham. September will be good for warm water temperatures.Enjoy exploring the Cape!

Last edited by HappyTrvlr; Mar 11th, 2023 at 08:42 PM.
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Old Mar 16th, 2023, 01:26 PM
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It has been a long while (used to live in New England before moving west) but have always loved Provincetown. It is truly unique. I'd probably spend even more time there. Of course depends your interests. But for "charming downtowns" truly Provincetown is pretty world-class!

Interested to hear what others think about the "play it by ear" as far as reservations for lodging in September. I would have thought it would still be too busy for that to work well??
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Old Mar 16th, 2023, 06:29 PM
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The Cape Cod National Seashore and towns it encompasses, from Chatham to Provincetown, is the most beautiful and unspoiled part of the Cape. One of my favorite towns on the Cape is Wellfleet. You could either spend several nights in Wellfleet, or definitely visit it for a day while in the area. There is great hiking/walking in Wellfleet, such as the Great Island trail. Two favorite Wellfleet restaurants are the Bookstore Restaurant and The Pearl. We also enjoy Winslow's Tavern for lunch and/or drinks. Their outdoor patio overlooks Main Street. Wellfleet is an artist colony with many art galleries and pottery shops.

In Eastham at the Cape Cod NS Visitor Center, there are walking and biking trails that takes you out to Nauset Marsh. Other good trails we have been on is the Fort Hill Trail and Red Maple Swamp Trail. You can find more information online, of course, or stop at a visitor center on Rt 6. They have tons of information including info on hiking and biking trails.

You should also visit the Audobon Society Wildlife Sanctuary in Wellfleet. There are some beautiful, easy, and flat walking trails there as well.

BTW, we live right next to Hopkinton! It's a lovely town and is where the Boston Marathon starts.

Last edited by KarenWoo; Mar 16th, 2023 at 06:34 PM.
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Old Mar 19th, 2023, 05:48 AM
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Thanks all for the recommendations!

I did a little looking into antique shops and it looks like most aren't actually on 6A, but closer to the northern and Southern roads like 28.

Think what sounds like the thing to do is follow 28 from Wood Hole to Chatham - taking detours along the way for a drive by the Kennedy Compound, stops in Hyannis, Harwich, and antique shops that look intriguing.
I imagine we'd arrive in Chatham near the end of the day, so maybe stay 2 nights there to get a taste of it before heading up the Seashore for hikes, views, pottery shops!, and a couple nights in Wellfleet, Truro or Provincetown.

Will look into accommodations in all those places -- if you have any favorite antique shops, I'd love to hear those too. Thanks again!
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Old Mar 19th, 2023, 06:11 AM
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I can't recommend any specific antique shops but I do know that there are quite a few in Brewster. You can google antique shops in Brewster. The problem with Rt 28 is that it is not an attractive or scenic route until you get to Chatham. Most of it is filled with commercial/retail properties, hotels, and traffic lights. Rt 28 is extremely crowded during the summer months so it is slow going. Not sure how crowded it will be in September. Rt 6A is much prettier and more scenic.

Perhaps one solution is to take Rt 28 when you leave Woods Hole, and then take Rt 6A when you start heading back to Boston. This would increase the number of antique shops you come across, and you will also enjoy the beauty and scenery of Rt 6A on your return.
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Old Mar 22nd, 2023, 03:39 PM
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Rt.6Ais charming,Rt.28 is not, it has shopping centers, light industry, more traffic.
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