Watch Hill, a classic New England resort town, has been a staple for vacationers in the northeast for decades. Even Taylor Swift has a house there. This town holds a special place in my heart because my late grandfather grew up here, and I have a lot of family history throughout southwestern Rhode Island. I hope that through the advice in this article, this region can become a special place for you too.

My Last Visit to Watch Hill and Southwestern Rhode Island

We began our journey from Sharon, Massachusetts, where my aunt lives. After a short morning drive we enjoyed a delightful breakfast at Sly Fox Den Too. I enjoyed their special of the day, the Bluefish hash, and found to my dismay that they were out of frybread. Despite this, Sly Fox Den Too provided a marvelous dining experience, after which we continued on to Watch Hill. My grandfather had recently passed, and I wanted to visit the same beaches he did as a child.

Upon arrival, we went to Napatree Point and enjoyed a leisurely beach walk through the dunes. Afterward we enjoyed an icecream cone at St. Clair Annex and returned to Sharon in time for lunch. All told, our morning excursion was a delightful and easy half-day trip. On my return, I would like to spend more time here and visit the Knickerbocker, a place where my grandfather used to play the saxophone.

What We Saw

The Tomaquag Museum – Located in Exeter, Rhode Island since 1958,the Tomaquag Museum is the only museum in the state dedicated solely to the history of the Indigenous peoples of Southern New England. This is an absolute must-see for people interested in learning about the Narragansett, a federally recognized tribe, and the original people of Rhode Island. Offering excellent tours, the price of $6 for an adult ticket is well worth it. Click here to find out more.

Napatree Point Conservation Area – Right in Watch Hill, Napatree Point Conservation Area covers 86 acres of conserved beachfront. The area was designated a “Globally Important Bird Area” by the National Audubon Society due to its importance as a habitat for species such as Piping Plovers. The Conservation area is open year-round for beachgoers and bird watchers, but it is important to follow the rules of respective enjoyment outlined here.

Where We Ate

Sly Fox Den Too – Sly Fox Den Too of Charlestown, Rhode Island is a treasure of the area, and one of few Native restaurants in the United States. With a small, diner-like atmosphere, you may not expect much from the food. However, Chef Sherry Pocknett (Mashpee Wampanoag), has become nationally known for her tremendous work here. Chef Pocknett even became the first Native American James Beard Award winner for her efforts. This is an absolute must-visit. Keep posted for my upcoming review of Sly Fox Den Too!

The Olympia Tea Room – Since 1916, the Olympia Tea Room has been an institution in Watch Hill. Described on their own website as “a wine lover’s seaside dream” the restaurant offers a great view of the harbor, particularly at sunset. With a menu of New England regional fare and a decided Italian influence, the Olympia Tea Room is a great representative of the local cuisine of Southwestern Rhode Island. While a bit on the pricey side, this establishment should definitely be considered when traveling through Watch Hill.

St. Clair Annex – What can I say? The St. Clair Annex is a local sandwich shop and ice cream parlor right at the beach. While I have only had the ice cream, I can report that it is made in-house and from quality ingredients. My $5 maple-walnut ice cream cone was excellent and more than worth the money paid.

Most Overrated

Watch Hill Beach – With a cost of $15 per adult for a single day’s entry, I could not in good conscience recommend Watch Hill Beach. Less than 100 yards away from the entrance to Watch Hill Beach is the entrance to the Napatree Point Conservation Area. You can do virtually all the same activities there for the modest sum of $0. If what you want to do at the beach falls within the rules of the conservation area, I insist you go there instead.

However, right at the entrance to Watch Hill Beach is a carousel that you should check out, especially if traveling with children. One of only two Dare carousels still in operation, the Flying Horse Carousel of Watch Hill was built in 1867, and has continuously operated at its current location for well over 100 years. Even surviving the great New England hurricane of 1938, the Flying Horse Carousel is the oldest “flying” carousel in the United States.