I will begin this post with a travel confession.
In the era of time we now all refer to as “Pre-Covid,” I had never spent quality time in Rhode Island. Shame on this New Englander.
As a Connecticut resident, I took my adorable neighbor – my stateside sister known for charming coastal towns and gorgeous beaches – a bit for granted. Friends whispered about Watch Hill, wanting to preserve its secrecy and I filed it away as a “we’ll go there one day” trip. When I finally did venture up I-95 in the summer of 2020, I felt like an older sister who got hit with the realization that her younger counterpart is actually quite cool. Maybe even cooler than myself. I suddenly wanted to hang out with her…all the time.
My family has now fallen in love with this quaint, yet punchy little town of Watch Hill - visiting multiple times over the past few years, and even drafting future dreams of one day buying a house there. And while the potential of being T. Swift’s neighbor is a fun thought (what a block party that would be!), the iconic pop singer’s house on the bluffs is not our inspiration for one day maybe relocating – instead, what we love is the town’s low profile reputation. This is not the Hamptons. This is not a boardwalk beachtown. This is a small, New England seaside village that doesn’t need the flair to be fashionable.
Whether you’re making family memories by walking the miles of golden beaches, meandering through the small boutiques, watching sunsets over Little Narragansett Bay, or driving the roads that duck in between historic homes, it’s obvious that Watch Hill is something special. This family travel guide to Watch Hill will detail everything you need to know about luxury accommodations, delicious New England restaurants, and the best activities to do with kids.
For your Planning Purposes
Getting there: Watch Hill is part of the larger town of Westerly, Rhode Island. It’s 3 hours from NYC, and less than 2 hours from Boston. There is also Amtrak service from Boston to Westerly.
Getting around: If you arrive by train, you’ll need to hire a taxi or Uber to get to downtown Watch Hill. If you have your own car, it will be easier to check out other beaches and restaurants in Westerly.
When to visit: This is a summertime hot spot – that’s when the town comes alive. Fall and winter are also popular, but many of the shops are closed for the season come wintertime.
What to do in Watch Hill with Kids?
Despite Watch Hill's small size, there's plenty for families to do. You could see it in 5 hours for a quick stroll and beach time, or could spend 5 days slowly taking it all in. Here were some of my favorite family activities.
Highlights if you're in a hurry!
- East Beach (near The Ocean House) - My friend, a proud Long Island native, once told me he thinks this beach (pictured above) is the most beautiful on the East Coast. This was a strong recommendation coming from “the competition,” and he did not lead me astray. East Beach is spacious, has very clean water, and is gentle enough to welcome young kids to play. It's also where you'll want to go for an epic sunrise.
- Explore the quaint town of Watch Hill - The small main street in Watch Hill is filled with boutiques, restaurants, and even the oldest operating carousel in the country! Begin by exploring the stores, which carry everything from summer beachwear, to home goods. Next, stop by St. Clair’s Annex for ice cream and then take a ride on the Flying Horse Carousel. It’s $2 a ride and an easy sell to a 3 year-old when you say it’s a magical unicorn.
- Watch the sunset over Little Narragansett Bay - On summer nights, you can find the whole town slurping ice cream from St. Clair's and watching the sunsets. The whole bay turns shades of orange, red, pink and purple, lighting up the fancy yachts and boats in the water.
- Hop on the Quonnie Queen boat at Weekapaug Inn - It's time to go cruising through Quonochontaug Pond! This salt water pond feels more akin to a small lake, and cruising through the waters in a 24-foot electric Elco boat was an awesome way to explore more of Rhode Island’s natural beauty. Tickets are $20/fare unless you are a guest at Ocean House/Weekapaug Inn/Watch Hill Inn, in which case it's complimentary
Don't Miss These Related Compass Roam Articles
Would you like to learn more about the best activities to do in Westerly / Watch Hill, RI? Here's an additional article you may find helpful for your family vacation to Rhode Island:
Luxury Accomodations in Watch Hill
There are 3 luxury hotels in Westerly (the larger town where Watch Hill is located) – The Ocean House, Weekapaug Inn, and Watch Hill Inn. As a guest in either one, you'll have access to amenities at all 3 properties. We stayed at Watch Hill during our first visit, but used the Ocean House beach, dined at the on site restaurants, and had access to their croquet courts, spa and more. We also had dinner at the Weekapaug Inn our first year, and returned as overnight guests the following year – so I actually feel like I’ve stayed at all 3! It’s no debate though that the crown Jewel is The Ocean House, and a review of Watch Hill hotels must start with her! This family travel guide to Watch Hill will detail what you can expect at each property, and why they are all family favorites.
The Crown Jewel
- The Ocean House - The Ocean House is the castle on Watch Hill. It screams Great Gatsby without feeling ostentatious – it’s laid back luxury, but with some slight swagger. The original building dates back to 1868, and underwent two major renovations: the first in 2010 and again in 2017. As you enter the Ocean House, you'll walk through a large wrap-around Victorian porch, filled with Adirondack chairs and people enjoying lobster rolls for lunch. The stroll down to the beach slowly rolls through the grassy lawn, featuring a croquet court and deck shuffleboard. It’s impossible to peel your eyes away from the hues of yellows dancing off the hotel. When you arrive at the shoreline, you’ll find yellow umbrellas dotting the entire sand, a beach-side restaurant, and the greatest waves for splashing. The Ocean House also has a 5-star spa, six restaurants and elegant hotel rooms. It’s the priciest of the 3, and most luxurious.
- Watch Hill Inn - On our first visit to southern Rhode Island, we were traveling with a 2 year old, and access to our own kitchen was a bit more valuable than a gorgeous 1 bedroom at the Ocean House. This sister property to the OH has residential style suites, each with modern conveniences like fully equipped kitchens and large living areas. Eagle's Nest room was incredibly spacious, clean, and comfortable. You’ll enjoy access to all the Ocean House amenities, but you’ll be located right next to Watch Hill village. Every room at Watch Hill Inn has front row seats to the sunsets that turn the whole bay stunning shades of purple, pink and red.
- Weekapaug Inn - When we returned the following year to southern Rhode Island, we chose to stay at the Weekapaug Inn and fell in love with the low-key luxury vibe of the resort. While the Ocean House feels like you’re staying in a wealthy estate, Weekpaug instead has the energy of an old-school beach club. A wide open grassy lawn overlooks Quonochontaug Pond, and the Atlantic Ocean is just a few minutes walk through the sand dunes. They have a gorgeous heated pool overlooking the salt water pond, with refreshing drinks and full service menu available. Families may want to check out the 1 and 2 bedroom suite options. We loved our stay in Piping Plover.
Delicious Restaurants in Watch Hill
Whether you’re looking for a quick bite to eat, or hoping to enjoy quintessential New England summer fare like lobster rolls and oysters, Watch Hill has something for everyone. Here are the most popular places to know about as you book your family travel to Watch Hill.
In Downtown Watch Hill
- 10 sandwiches - This local favorite cafe sources fresh ingredients to make their killer sandwiches -- these are perfect to take to the beach! Lines are long come breakfast time, but it’s also a popular spot for lunch and dinner. As an added bonus, if you stop by during happy hour the menu features different flatbreads and oysters too.
- Sift bake shop - I can still taste the savory spinach feta croissant that came from this treasured local bakery! The labor of love that goes into each scone, cookie, croissant and baked good hits you with the very first bite. In fact, head pastry chef, Adam Young, was named 2018 “Best Baker in America,” by the Food Network! If you’re staying at Watch Hill Inn, Sift is located right down the road and is perfect for buying a to-go breakfast to enjoy in your room. There were quite a few mornings I kicked my hubby out of bed to beat the line before locals and tourists alike descended upon my savory croissant. The baked goods sell out fast so the early bird will definitely catch this worm!
- Olympia tea room - Every town has “that restaurant” that everyone knows about – people come for the food, the drink, and the energy. At Watch Hill, that award goes to family-run restaurant Olympia Tea Room. Here you’ll find a bistro-like menu with favorites like fish and chips, burgers and oysters. My favorite dish was the roasted clam linguine. In addition to the good food, the restaurant has one of the best sunset views in town! If you’re one of the lucky ones who snags an outdoor seat at sunset, you’re in for a special experience.
- St. Clair Annex- This family run ice cream and sandwich shop has been in the neighborhood since 1887! That’s a lot of scoops! Chances are, if you’re in town on a summer night and you see kids running around with ice cream cones, it came from Clair’s. Grab yourself a cone and watch the sunset over Little Narragansett Bay.
- COAST - Many of Watch Hill’s restaurants are kid friendly, but this one you may want to save for a special date night. The chef designs the 4 course menu that day, based on the seasonal ingredients available. If you do wish to bring the kids along for this culinary journey, keep in mind there is a minimum age of 8.
- Verandah Raw Bar- When you pull up to The Ocean House, you’ll instantly want to plop on the porch for a refreshing lunch. The Verandah Raw bar is only open during the summer months and features a seafood-centric menu.
- Del’s homemade frozen lemonade - There’s nothing better than frozen lemonade on a hot summer day! This refreshing slushie is as famous in the community as The Ocean House. Their lemonade trucks are located throughout Rhode Island, and many local shops will have Del’s on hand.
Restaurants Within A Close Drive
Watch Hill is part of the larger town of Westerly, where there are some other culinary treasures you’ll want to make reservations for.
- Cooked Goose - The Cooked Goose is the most popular brunch spot in town. If you’re headed here, expect to have a wait of at least 30-45 minutes. With a 2 year old in tow, I wasn’t feeling particularly brave enough to endure the line, but good friends swear by this spot.
- Ella’s- This fine dining establishment is known for its outstanding French-Asian inspired cuisine. Make sure to book your reservation as soon as you can!
- Matunuck Oyster Bar - Located slightly outside of Westerly (25 min drive) is the very popular Matunuck Oyster Bar. Enjoy fresh oysters raised on their own farm, while overlooking Putter Pond and watching the sunset. Reservations are a must!
- The SeaRoom - Our favorite meal (both years) was at this relaxing family restaurant at the Weekapaug Inn. Even though the menu is described as “casual New England cuisine,” every dish seemed elegant and refined. As an added bonus, my toddler loved the food too! Reserve a table ahead of time, and ask for outdoor seating with views of the pond.
Tips for traveling to Watch Hill
- Make you summer reservations early - This tiny town books up fast! If you’d like to visit during the summer months, it’s best to reserve as soon as possible.
- Parking is limited - As a hotel guest at the Ocean House, Weekapaug, and/or Watch Hill, you’ll have access to their parking lots. However, if you’re passing through for the day, you’ll quickly notice there isn’t a lot of street parking in downtown Watch Hill. In fact, there are only 6 free all-day parking spots! Most of the street parking is a 2 hour limit. I'd recommend parking in a paid lot ($20) if you don't want to leave the beach to move your car. There's also a reservation based lot at 44 Bay Street. Call 24 hours in advance at 401-315-5500 to reserve.
- Take it slow - Watch Hill is a quiet town where the day is about strolling the beaches on a morning walk, enjoying leisurely meals, splashing in waves, and slowly exploring the village. If that’s what you’re looking for, then it’s the perfect spot for your family to visit.
Day Trips From Watch Hill
While it’s easy to fill a 4 or 5 day vacation at Watch Hill by simply relaxing, there are a few day trips worth considering if you’d like to switch up your surroundings. We visited Mystic on our way home to CT. We also spent an afternoon wandering through Newport. Both towns are worth checking out on your family trip to Rhode Island.
Mystic is another coastal New England town that will capture your heart. Start by exploring the historic main street, filled with boutiques and restaurants. I recommend Bravo Bravo for lunch or dinner. For kids, check out the Mystic Seaport Museum or impressive Mystic Aquarium. Lastly, in Stonington, CT, you'll find Stone Acre Farm, which is a 63 acre garden. In the summer months there is often a pop up restaurant.
I went to Newport for a few hours and wish I had booked a few days! This charming town has the quintessential seaside harbor feel – yachts fill the docks, oyster shacks line the walkways, and nautical themed stores beckon you to come browse. You’ll want to be sure to explore the downtown and later do the Cliff Walk, where you can see Gilded-Age mansions lining the water. When your day of touring is done, have dinner at The Mooring – their clam chowder hits the spot on a summer day.
That's a Wrap
I still can’t believe it took me years to discover the beautiful beaches, fantastic food, and delightful local communities of Rhode Island. However, now that we've visited, I know our family will be addicted to return for years to come. If you haven’t yet made your way to the southern section of the tiniest state, it’s time to book your trip now.
I hope this article has inspired your own family getaway to Watch Hill, Rhode Islandl. If you have any questions, or your own travel tips, please leave them in the comments below. Also, don't forget to sign up for the monthly newsletter, packed with travel tips, upcoming news, and access to FREE destination itineraries.
Start gathering your future travel ideas now! Sign up to receive exclusive travel itineraries and tips.