Wentworth Coolidge Mansion is historically significant as the only original surviving residence of a Royal Governor in the United States. It also served as an artist colony in the 1800s and attracted many notable talents including John Singer Sargent, Beatrix Potter, Edmund Tarbell, and Isabella Stewart Gardner. The Mansion is also nearly the backyard of Molly's parents' home. Molly is the 4th generation to live on Martine Cottage Road (off of Little Harbor Road). If you feel like going on a brief hike, check out the Little Harbor Trail that spans the waterfront, with views of the Wentworth by the Sea Hotel in Newcastle, and brings you through the Wentworth-Coolidge and Creek Farm properties.
Simple and delicious ice cream joint on the Rye/New Castle border. Pro-tip is to grab ice cream on the way back from Wallis Sands Beach or cruise over to historic presidential hotel, Wentworth by the Sea Hotel, and check out all the yachts docked at the marina.
There are so many great breweries in and around Portsmouth. Liars Bench is popular and in walking distance from downtown. You can find more options here: https://www.goportsmouthnh.com/craft-breweries/. We've also listed a couple other options in North Hampton/Hampton that are worth the visit.
Kittery Foreside has a great little selection of restaurants and shops. Molly's favorite store is FOLK - natural wine, cookbooks, and great selection of housewares. Joe loves a cocktail from Wallingford Dram. Also nearby (in addition to Lil's), Maine MEAT, a really special whole animal butcher; Black Birch, a restaurant and fun bar with elevated pub food; Anju, a fantastic spot for ramen and okonomiyaki (japanese style pancake); and, a little further down the road, Loco Cocos Tacos, which serves great southern California-style mexican and strong margaritas.
The wait is worth it at Lil's. The crullers are fantastic (& NYTimes famous) but all their baked goods are special. Molly is a big fan of their olive sourdough bread. Lil's also recently opened a sister spot, The Islander Cafe, 52 Main St, New Castle, NH 03854.
Lots of great outlet options if you are inclined to do a little shopping. Check out Joe's favorite, Lululemon, or Molly's favorite, Crate and Barrel.