Massachusetts vacation ideas?

never been to Massachusetts, but dreaming of going in October.  sick of this hot steamy Virginia summer.. I want New England fall!! (obsessed with fall) thinking 5-6 days

I know it’s not the best time, but I really need this getaway.. I understand we have to get a Covid test less than 72 hrs before entering MA and have negative Results printed out to carry with us everywhere to avoid quarantining (I’ll look into where we can get that done.)  in VA were also used to wearing masks most places. 

Anyway I know nothing about Massachusetts.. I need ideas.. if weather is nice (which for me means anything between 45-70 then  we would love to do some nature stuff.. see the leaves, better for social distancing. We’re not into overly crowded type places anyway.. 

Things I’d love to do

1) Whale watching 

3) Cape/beach

4) cute old towns with lots of brick or stone, picturesque places you know..

5)  Also a big history buff and would love to check out Salem and some other Colonial era history (Realize for that we may have to put up with more crowds/tourists) 

6) nature stuff..not into strenuous uphill hikes but “walk in the woods” type hikes are fine. 

 We’d like some “hidden gems” and to avoid overly touristy /crowded places. Is Cape cod real “busy” in early October? 

Any state park like places not too far from Salem?  especially ones that may have cabins for rent? (we’d like to keep things within a 2 hr driving radius of Boston (where we may fly into)  

Any suggestions at all?  

5 Answers

  • 3 months ago
    Favorite Answer

    Fall in New England is beautiful- it's my favorite time of year to visit home.

    While I love the Cape in the fall, be warned that not everything will be open.  It likely will not be very busy, though there will be people there.  When you say "beach," do you mean actually lay on the beach and swim?  It won't be the right weather for that.  Fall is a good time for walking the beach wearing warm clothing, looking for shells, etc.  I doubt anything will be happening this year, but you can check to see if any of the fall festivals are actually going on- there's usually a cranberry festival in the Wareham area (right before the Cape bridges) and usually a festival in Yarmouth over Columbus Day weekend that includes fireworks on the beach.  However, I am doubtful that any of those will actually be held this year due to the pandemic.

    If you bike and you're heading to the Cape, I do recommend checking out the Cape Cod Rail Trail.  I love this in the fall.  You'll ride past several different kinds of areas, including cranberry bogs.

    Other Cape ideas- Cape Cod Canal (biking or walking), Truro Vineyard (far though, but offers a great wine tasting and they are currently open), Chatham fish pier (watch the boats come in and unload, watch the many seals, get takeout from the fish market), the National Seashore (depending on what's open.)

    Please be aware that Salem has canceled many of its typical October events and may not have many of the sites open due to the pandemic.

    If you have never been before, I would recommend doing one of the typical tourist things... walking all or some of the Freedom Trail in Boston.  I found it tedious and boring as a child (when you grow up in the area, it's a common field trip!), but as an adult who has moved away, I miss being surrounded by so much history!

    Other ideas...

    If you're going to Salem, explore more of the North Shore area and maybe Cape Ann (though not sure what will be open/allowed in the fall.)

    Because you mentioned a "walk in the woods," why not go old school walk in the woods and check out Walden Pond, where Thoreau probably did his best thinking?  It's a state reservation, so make sure it's open before you go.

    If you have a full day, you might want to consider a drive out to western Massachusetts, to the Berkshires (gorgeous fall out there!)  Some of the ski resorts run scenic chair lifts and alpine slides in the fall, though I'm not sure if that will happen this year.  If you're driving from western Mass to eastern Mass or vice versa, check to see if the Big E drive-through bakery/food event will be running in Springfield.  The Big E is a huge New England fair that happens every fall, but has been canceled for this year.  However, they've been doing the fair special foods on certain days in a drive-through bakery kind of format.  I don't know what dishes they're serving, but the Big E is known for having a building of each state (not just dedicated to the state, but the building itself is considered to be in that state, so even though the fairgrounds are in MA, you can visit all six New England states in less than ten minutes), and each offers a food from that state.  If you're driving through anyway and the food event is running, might be worth a stop!

    You could also head up to the White Mountains area of New Hampshire.  The Kancamagus Highway is a scenic route through the area.

    In areas away from the major cities or Capes, visit a local apple orchard.  I have lived outside of New England for over 15 years and still think New England apples are THE best.  Ordinarily, I'd tell you to check out any area's local social media or website to find out about fall festivals, but I'm assuming none of those will happen this year.

    Take a drive up to southern Maine.  Visit a rocky Maine beach (York is about an hour and twenty minutes from Boston.)  Get some seafood.

    Do keep up with current restrictions and double check as it gets closer.  Right now, I believe most of New England is okay to travel within from the New England states, though Massachusetts may still be restricting Rhode Island.

    ETA: To address the quarantine comment in another answer, CT does not require people coming from EVERY state to quarantine (people from NH, VT, MA, ME, RI, NY, and NJ do not, as well as a handful of other states.)  Depending on the day, people from about 30-35 states need to quarantine.  Massachusetts usually has one more state than CT (CT took RI off the list recently, but MA kept it.)  Check the actual state you're visiting for the requirements.  Some states are accepting a negative test within 72 hours of arrival, but they usually require the PCR test and NOT the rapid, so keep that in mind.  Maine accepts the test, CT and MA have wavered on it and I'm not sure of their current requirements.  It sounds like the original asker has already looked into that and knows that the test is valid in lieu of quarantine.  My advice would be as I said above, just stay current on restrictions as they change frequently.

  • 2 weeks ago

    Dont go it sucks

  • Cape Cod traffic typically falls off after Labour Day weekend, but keep in mind that some restaurants and shoppes close by October.

  • 4 months ago

    If you are flying into Boston and you are a big history buff, then definitely do the historical stuff in Boston associated with the Revolution.  If crowding inside the buildings is a concern (or things are closed), then just walk the "freedom trail" from Boston Common to Bunker Hill.

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  • Cammie
    Lv 7
    4 months ago

    Here in CT, right next to Mass, anyone coming from another state must quarentine for 14 days.This is a pandemic that will not be over by October.Nothing is open.

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