After some intensive online research, I can say with some degree of certainty that Henry Ford, Clark Gable, & even Albert Einstein all summered in Watch Hill at one point or another back in the day. (Also, if you have never seen any Clark Gable movies, time to start stalking TCM for It Happened One Night, co-starring Claudette Colbert, who was the Julia Roberts of that era to Gable's Clooney.)

Okay, if you’re looking to experience a bit of WH Classic circa 2020, please know that all your old favorites are open and and waiting for you. Now, let’s dive into these top shelf destinations “in town.”

1. The T-Shirt Shop Across From The WH Yacht Club

Every summer we load up on tees and pullovers from this little shop set back from Bay Street — because you can never ever have enough to throw on after a day at beach, when it gets chilly at night, et cetera. It is filled with great hang around gear! In addition, they usually always have some kind of sale going on.

2. Sift Bake Shop

More of a new classic, Sift opened their Bay Street outpost a few years back (their award winning original bakery being situated in nearby Mystic) and it has since become known not only for outstanding iced beverages but also for delectable pastries and sweets such as blueberry muffins (which were sold out the other afternoon when we were placing an order), cookies, chocolate croissants (also sold out that same day), and more. These days they are taking orders outside the front entrance and then have them ready and waiting in the doorway asap.

3. This One’s For The Little Ones

Children’s books were not on my radar really, until, that is, my grand or great nieces and nephew came on the scene. Now I’ve rediscovered The Brass Ring, a picture book written and illustrated by prolific kids book author Nancy Tafuri, spotlighting the fabled Flying Horse Carousel in WH. (She has something like 50 titles to her credit including her most famous one, Have You Seen My Duckling?) If you’re looking for an autographed copy for the kiddo in your life, you will want to pop into Gabrielle’s Originals (right near the t-shirt shop I spoke of above). It’s such a special gift for that family that loves Watch Hill.

4. St. Clair's

We've already made multiple trips to the iconic St. Clair Annex for homemade ice cream this season. (No one ever says Annex in real life btw.) Family owned since 1887 — practically unheard of in this day and age —they’re also keeping up with the times, having added eats like avocado toast and Impossible Bugers to their menu over the last few years. One call-out, though, is that they only take cash, no cc’s or debit cards, but there is an ATM inside, so no need to freak out.

5. Olympia Tea Room

Long before it was featured in Vanity Fair in 1996, in a piece celebrating its 100th year in business, the Olympia Tea Room was the place for eats and drinks in Watch Hill. With its art deco interior, the pink walls and ceiling, that black and white retro tile floor, and paintings by one half of the husband and wife team who own and run the place lining the walls, it always felt (to me) like stepping into an old Hollywood movie, as though Bogie and Bacall, along with maybe Peter Lorrie or Sinatra in tow, were going to glide thru the screen door and slide into a booth any second. For summer 2020, the Tea Room is indeed open for your next lunch or dinner, the only difference is that there are fewer tables inside and out front, in keeping with current Phase 3 rules and regulations for restaurants.

That’s all for now…

Stay cool.

***This post has been updated and revised from one that appeared previously on this site.***