It's not super close to Wellfleet but I LOVE the Sandwich Glass Museum... and Sandwich itself is a charming little town - it's also the last weekend for the walking tour of the town they offer. If you are into that sort of thing and go, I highly recommend you get there early enough to see the glass blowing demonstration... the woman who was there when I went was fantastic and if you go to the last demo of the day, she attempts a very very large piece (often does not work but you get a good discussion about why etc). Anyway I am a real glass person so I loved this. If you like architecture and lighthouses, I would look into lighthouse tours - there are a ton around here. Not sure what their hours are... Columbus day is kind of the last big hurrah around here before the seasonal stuff closes down for the winter. Not sure if any of the whale watching cruises or stuff like that is going on. I don't know the cape all that well but I moved to Martha's Vineyard almost a year ago. Fall is my favorite time here but that is because things quiet down! It's beautiful here on the island and might make a nice day trip but a lot of stuff is closed down right now - but there are still walking trails with gorgeous views, downtown Vineyard Haven has a lot of stuff open year round and some of my favorite restaurants are open year round. The ferry ride is also really nice! If you come to the island I can give you some pointers on that.

Cute house! I'm concerned that you are piecemealing changes without considering a whole plan - even if that whole plan is not one you can enact right away. My order of operations would be new roof, new front door then wait until you can afford to redo the stairs and railing together. In the meantime, just paint the stairs and railing. Stacked stone facing will not work at all with the style of your house and with the lines in your siding. I think it will appear to be a stuck on after thought. You can certainly choose elements to give your home a more contemporary feel, but a stacked stone look will not be a good one. With bluestone, consider your roof color. What color will your roof be? When you do more landscaping work, be sure to consider a base of evergreens mixed with other seasonal shrubs, trees, and plantings. This way your home will look great even in the winter months.

depends on what you want. place kitchen over on the right ....at the rear of living room...place a dining zone near fireplace and rest of that big room add some living room furniture. Turn the existing kitchen into an entry vestibule but give a foot or so back to the "dining room " so it can be a parlor or small living room if you want. if you remove the walk through kitchen that you now have maybe the half bath could be renovated and get a shower stall so the study can be an ensuite bedroom someday. a table or banquette along with kitchen on the right side . but not sure what you really want to do....the existing kitchen w walkway down the middle is like a closet or mudroom / very constrained ....you have spaces but what scope of reconfiguring things has your interest?

This is a Georgian Revival house. The shape is the same but the proportions and the formal details are different, a "Cape Cod" would generally have plainer detailing, a steeper roof, and usually do not have so much space above the windows and doors and the eaves. A Cape Cod would have proportions and details more like the side wings of your house, and not have the brick jack arch headers over the four main windows, the arches on the dormers, or the broken pediment over the door. Since a Cape Cod is a more generic form (and practically anything 1-1/2 stories tall with a symmetrical form gets labeled a "cape cod"), they can be modernized somewhat and still look okay, but I don't think it's very successful to try and take a house with so many classical details and attempt to turn it into something else, especially just by painting and putting in the wrong windows. I live in a city with genuine 18th and 19th century houses and it seems like people spent the 1880s to 1950s trying to turn a lot of the facades into something else and then from the 1960s and 1970s and beyond trying to put back together what had been messed up with previous modernizations. The last AI picture which keeps the house a Georgian Revival but painted white, is not to bad but the first one that paints out all the details of the house and obscures the details in the space above the doors and windows, and the second one that puts thick black outlines around everything are both pretty awful. Are they current and fresh and very 2020s? Yes. But they are like a 75 year old woman who is in great shape trying to dress like her college age granddaughter. She would look great if she acted her age, but looks silly trying to be something she's not. The black and white is more a scheme for a house like Celery shows, which is a completely different style of house. Personally I would put on better shutters and a fresher trim color and that's it. You can decorate however you want on the inside. (You can on the outside too, but it just won't be as successful).