Bar Harbor

Quebec
Acadia National Park and Bar Harbor, Maine
Chicago

Cabo is beautiful and packfic coast is so much cooler.

Nantucket, Park City, Telluride, Aspen, Crested Butte, Big Sur, Newport, RI, Carmel

Anonymous wrote:Portland, Maine

Or Boston. Portland feels like it doesn't have all that much to do. Maybe I'm wrong.

Great food and location though.

Martha's Vineyard
Niagara on the Lake, Ontario

Portland, Maine

I’d go to the Hamptons. Crowds are gone, September weather is usually wonderful, prices come down. Hard to beat.

I am two years away from you and will spend my first September vacation in Cape Cod. Bliss - cool temps but beautiful blue skies. All the crowds are gone.

Consider Primland for a few days, if within your budget. You can drive, saving the cost of airfare.

https://aubergeresorts.com/primland/

Adirondacks or Berkshires

Twins are headed to college in August and DH and I are looking for a long weekend (maybe week long) trip in September as first time empty nesters. Caveats - can't be too pricey (have a trip to NYC planned for Thanksgiving and a trip to Florida in Jan - plus college tuition.) We want to both relax and do stuff (ie. not sit at the beach all day.) And I am going through menopause, so would like to avoid crazy heat if possible (I am meltiing in DC these days!!) We do have a ton of Southwest points.

Suggestions are welcome!