Road Trip through Coastal New England & Long Island

by KidTripster Staff
Bridge open to let boat pass beneath it in Mystic

6-day road trip for a young family to soak in the beauty & history of this coastal region

Driving through the small states of Southern New England – Rhode Island and Connecticut – takes little to no time, giving you plenty of opportunities to really experience the history and beauty of this area.  As an added bonus, we drove the car onto a ferry to easily reach Long Island (and avoid New York City traffic!). My kids, 5-year-old twins, loved this trip. There was minimal time in the car and lots of exploring.

Exterior of The Whaler's Inn
Photo: The Whaler’s Inn

DAY ONE

What to do?

We started our journey with an easy drive from Boston to Providence, Rhode Island – home to the Roger Williams Park Zoo (1000 Elmwood Avenue). While the weather was dreary, the upside was no lines, no mobs of people, and no straining to see the animals. Instead, we walked leisurely throughout the entire zoo.  We took advantage of the informative zookeepers’ talks. At the cheetah station, it was just the four of us with a zookeeper, so we asked lots of questions and learned lots of cool facts. For example, did you know cheetahs can hit speeds of nearly 70 miles an hour but can only race after prey for 30 seconds? We visited the zoo for five hours, spending extra time with the harbor seals, giraffes, and camels. Cost: Youth (Under 2) Free; Youth (2-12) $9.95; Adult $14.95.

KidTripster Tip: Although my twins are 5 years old, we decided to rent a double stroller in an effort to see everything more easily. It was really more of a wagon/stroller combo than a traditional stroller, where they could pop out easily at the exhibits. Rental cost: Single $5; Double $7.

KidTripster Tip: Roger Williams Park Zoo is an AZA-accredited zoo that participates in the Reciprocal Admissions Program. If you are a member of an AZA-affiliated zoo or aquarium, you may eligible for discounted tickets. Check with your membership office or online.

Where to eat?

Because of the weather, many of the kiosks were closed including the beloved Dippin’ Dots kiosk.  We ate at the Serengeti Market Cafe with plenty of kid-friendly choices including hot dogs, macaroni and cheese, and chicken fingers. There also are salads, wraps, and chili on the menu. For our family of four, lunch ran about $40. You can bring food into the zoo; pick a table or bench and enjoy your lunch while watching the elephants.

Where to stay?

From the zoo, drive 45 minutes south to Mystic, Connecticut and check into The Whaler’s Inn (20 E. Main Street). This five-building, 48 guest room hotel – just steps from the ocean – is a beautiful mixture of the past with tin ceilings in the hallways and the present with a Roku-enabled television in each room. At check-in, grab a few complimentary chocolate chunk cookies in the lobby. We booked the Junior Suite in the main inn, which had an ultra comfortable, queen-sized bed in the main room and kid-sized bunk beds in what was likely a dressing room a century ago. And both my husband and I and the kids had our own televisions, so no fighting! The kids were so excited to sleep in bunk beds and be in a separate room from us. Rates start at $119/night; a breakfast of fresh pastries from Sift Bake Shop, yogurt, and oatmeal is included.

Where to eat?

The friendly hostess at the hotel, Erica, suggested her favorite, Pizzetta (7 Water Street), for dinner. Just a short walk from the hotel, it’s a cute, cozy restaurant on the first floor with a bar and take-out counter in the basement. It serves delicious pizzas, sandwiches, and salads including gluten-free and dairy-free options. If your kids are too tired for their active day, order dinner to go.

Beluga whale at the Mystic Aquarium
Photo: Mystic Aquarium

DAY TWO

What to do?

If you’ve ever heard of Mystic, you’ve likely also heard of the Mystic Aquarium (that, and the 1988 movie Mystic Pizza.  Yes, that’s a real pizza shop here!).  It’s a world-renowned aquarium (55 Coogan Boulevard) that features Beluga whales, penguins, sea lions, sharks, and other marine life. Our first stop was to see the Beluga whales. They are beautiful creatures that were quite playful with the younger one even splashing visitors standing up against the glass. Inside the main gallery, we were greeted with a shark touch tank manned by a well-informed volunteer who was able to answer all of our questions and supply additional information that we didn’t even think to ask. Also inside the main gallery, you’ll find jellyfish, tropical fish (think Dory and Nemo), and stingrays. 

The aquarium also hosts special exhibits. We visited one about frogs. Both kids had a blast going from display to display, trying to find all of the frogs. They’re tricky and can camouflage themselves quite well.

I’d recommend catching one of the 20-minute sea lion shows. The three sea lions parody many of the channels that you find on television (think ESSeaN and SealTV). At the end, the sea lions come onto the walkway in front of the audience, so try to get there early for seats near the front.

Because we had the value ticket, we were able to take in a 4D movie. It had nothing to do with the aquarium, as it was The Lego Movie, but my kids enjoyed it all the same. Nothing like getting sprayed with lemon-scented water while wearing 3D glasses!

General admission cost: Youth (2 & under) Free; Youth (3-12) $25.99; Youth (13-17) $29.99; Adult $35.99. Value ticket cost (includes 4D movie and seasonal exhibits): Youth (2 & under) Free; Youth (3-12) $31.99; Youth (13-17) $35.99; Adult $41.99.

KidTripster Tip: Check with your hotel to see if it offers packages with discounted tickets.

Where to eat?

Penguins Cafe at the aquarium is a small dining area with limited indoor seating but more outdoor tables available.  It serves your typical hot dogs, hamburgers, chicken fingers, and pizza by the slice, plus wraps and salads. You can’t bring food into the aquarium, but you can get your hand stamped, if you decided to leave for lunch.  There are picnic tables just outside the entrance. 

For dinner, check out Captain Daniel Packard Inne (32 Water Street), a Mystic classic. The Inne was built on its present site along the Mystic River more than 250 years ago. Nowadays, the Inne has plenty of character and offers live, local music on many nights. The food was delicious, and the staff didn’t balk at dietary substitutions. There’s also a kids’ meal available. While the kids opted for grilled cheese and chicken fingers, we selected the Red Curry Stir Fry and Black Pepper Crusted Blackjack Sirloin. We weren’t disappointed. 

Exterior of Bridghampton Inn & Restaurant
Photo: Bridgehampton Inn & Restaurant

DAY THREE

What to do?

After another delicious breakfast at The Whaler’s Inn, head west about 30 minutes to the Children’s Museum of Southeastern Connecticut (409 Main Street) in Niantic. It’s an adorable, interactive museum best suited for younger children, perhaps up to 7 years old. The museum has a replica fishing boat, complete with life vests and buoys to drop overboard into the “water,” a fire engine with working lights and siren along with firefighting suits and the all-important hats, a market-restaurant where children can shop for produce and then spend time in the kitchen “cooking,” and a designated toddler area with toys and space for the youngest visitors. The museum also has a Discovery Room, where my children loved playing Hot Cross Buns and Twinkle, Twinkle on the pipe organ, designing pipe runs for golf balls, and making colorful designs with a giant Lite Brite. They also got to meet Lady Waldorf, the bearded dragon, Mr. Rogers, the Russian tortoise, Hip and Hop, the Australian tree frogs, Loki the Leopard gecko, and Cranky and Crusty, the land hermit crabs. Yes, we learned all their names! We spent about two hours at the museum, popping from space to space, often going back to revisit a favorite area. Cost: Youth (1 & under) Free; Other $7.

Where to eat?

You’ll work up quite an appetite at the children’s museum, so walk across the street to Cafe Sol (346 Main Street).  The kids ordered grilled cheese and a cheese quesadilla (order the smaller kids’ size). The restaurant also has a full selection of sandwiches and salads with many vegetarian and vegan offerings. It’s all made-to-order and very tasty. 

After lunch, walk just a couple of storefronts down to Gumdrops & Lollipops (334 Main Street) for some ice cream. The store is designed like a 1950s diner and has an extensive hard ice cream menu as well as several soft ice cream flavors. But to get to all of that, your kids will have to walk by a long display of candies, jelly beans, chocolates, and fudges.  Good luck!

KidTripster Tip: Looking for a way to burn some kid energy? Take a walk on the boardwalk that runs behind Main Street and along the water.

Where to stay?

Now head across the Long Island Sound to Bridgehampton, New York, for the night.  You can catch the Cross Sound Ferry (2 Ferry Street) from New London, Connecticut to Orient Point, New York. It’s about a 1-1/2-hour ferry ride. The kids were excited to get out of the car and head to the top of the ferry. It can be a bit windy up there, so bring a sweatshirt. And you’re not allowed to go to your vehicle while crossing the Sound, so be sure to bring any snacks and chargers when you get out. Reservations are encouraged, though we were able to change our reservation just a few hours before departure without a problem. Cost: starts at $55/vehicle; additional fees per passenger.

There are two ways to get to Bridgehampton from Orient Point. You can drive around from the end of one point to the end of the other. It’s a long drive on a two-lane road, which can become longer depending on traffic. Or you can drive south to two additional ferries. These ferries only accept cash or check and depart every 10 to 15 minutes.

After the fun journey, we arrived at The Bridgehampton Inn and Restaurant (2266 Montauk Highway). The 12-room inn dates back to 1795 and sits right in the middle of town. Our room included a king-sized bed; once again, the kids had their own space separated by pocket-French doors.  In their room, there was a daybed and trundle bed.  My son thought this was amazing.  “I get to sleep in a drawer!” he exclaimed.  It was all impeccable and such a beautiful mixture of modern style and historic charm.

Where to eat?

Make the short walk from the inn to World Pie (2402 Montauk Highway) for dinner. Here you can select between many specialty pizzas as well as salads, sandwiches, and other entrées. The kids ordered a half cheese-half pepperoni pizza.  My husband and I ordered lamb chops and a chicken salsa salad. We couldn’t have been more pleased with the service and food.

Aerial view of the Montauk Point Lighthouse
Photo: Montauk Lighthouse Society

DAY FOUR

What to do?

The Bridgehampton Inn & Restaurant serves a delicious, complimentary breakfast. The kids chose pancakes; my husband and I selected eggs. There’s also fruit, yogurt with granola, and an assortment of pastries.

We didn’t have a set itinerary for this day, but after enjoying breakfast on the patio and looking for bugs in the garden, we decided to drive 45 minutes to Montauk Point State Park (8 Old Montauk Highway) at the end of Long Island. We’re so glad that we did! After playing on the playground, we walked to Montauk Point Lighthouse. It was commissioned by President George Washington in 1792, making it the first lighthouse in New York. You can purchase tickets to the museum which also allows you to climb to the top. Cost: Youth (12 & under) $4; Adult $11.

The museum is designed to give you an idea of what life was like for the lighthouse keeper. There’s also an interactive diorama of lighthouses in the area with fun facts about each one. The walk to the top is 137 steps, but you can stop along the narrow spiral staircase, if needed. My 5-year olds had no problem making the climb. At the top, step out onto the small landing to see much of Block Island Sound and the Atlantic Ocean.

KipTripster Tip: Anyone who wants to climb the lighthouse must be at least 41-inches tall; no exceptions.

After the climb, run down one of the marked trails to the beach and check out the stones and shells. You’ll likely see fishermen down along the beach, too.

Where to eat?

The town of Montauk has a plethora of restaurants ranging from delis to upscale, white-tablecloth restaurants.  Because of the popularity of fishing in Montauk, it’s a good place to order fresh fish or seafood.

Where to stay?

Montauk is home to several bed-and-breakfast inns as well as motel-style, beach resorts.  In the summer season, these places fill up quickly. If you visit in the off-season, you’ll enjoy lower prices and more availability.

Instead we headed west to Hauppauge and booked a room at the Holiday Inn Express  (2050 Express Dr. South). The kids were happy to see a pool and a pancake-maker machine at breakfast!

Fire island lighthouse with boat sailing in water
Photo: Fire Island Lighthouse Preservation Society

DAY FIVE

What to do?

On your last full day of vacation, head to Fire Island Lighthouse (2050 Express Drive South).  Fire Island is an outer barrier island on the southern shore of Long Island. On the western side of the island, you’ll find Robert Moses State Park. You can park in any of the lots, but Lot 5 is the closest to the boardwalk and lighthouse. Parking cost: $8-$10, depending on the time of year.

On the walk to the lighthouse, keep your eyes peeled for wildlife. We saw two deer and family of foxes including several pups. My daughter was amazed that she could be so close to a deer without it noticing her. And the fox pups got a big “awww” from everyone. Fire Island Lighthouse is part of the National Park Service and maintained by a non-profit organization, Fire Island Lighthouse Preservation Society, which includes three staff members and 154 volunteers. The lighthouse is open year round, but in July and August, there are more kids’ programs.

Here another lighthouse climb awaits you, oddly enough with the exact same number of steps – 137!  But unlike the Montauk Lighthouse, this one has five platforms along the way with windows looking out at various points. Each platform has a sign outlining what step you’re on, how thick the walls are at that point, what you’re seeing, and interesting facts about the lighthouse and surrounding area.  Cost: Youth (12 & under) $4; Adult $7.

KidTripster Tip: At the top, you’re able to walk around the entire circle, but be careful, as it can be incredibly windy.  The views are incredible, and on a good day, you can see the New York City skyline.

Once you descend, take some time to visit the museum. More than 6,000 schoolchildren visit the lighthouse and museum every year, and the Society does a great job of programming. On the second floor, they run a rescue operation, recreating what would have happened if a ship ran aground offshore. My kids thought this activity was a lot of fun and were so glad that they were able to rescue the teddy bears who acted as stranded passengers. 

Once you’re done in the main building, head out to the boat house, where you can check out some of the rescue equipment that crews used in the 1800s and early 1900s. And don’t miss the lens building, where you can see the original Fresnel lens used in the first lighthouse; the original light was rebuilt because it was too short.

KidTripster Tip: The Society and its volunteers are dedicated, and the programs they provide are fun, informative, and interactive. Check out the schedule in advance.  

Where to eat?

Robert Moses State Park has several concession stands with typical hamburgers, hot dogs, and chicken fingers. Alternatively, pack a picnic lunch. Bring along a blanket and enjoy some beachcombing along the white sand.

Ferry from Bridgeport, Connecticut

DAY SIX

Getting home

Time to head home. You can take one more ferry in order to avoid the New York City traffic and extend the fun a little bit longer. The Bridgeport & Port Jefferson Steamboat Company operates out of Port Jefferson and connects to Bridgeport, Connecticut. Reservations are suggested, though we didn’t have any when we arrived mid-day an hour before departure, and we were able to get on without a problem. The ride is about an hour and 20 minutes and has the same snack bar set-up as the previous ferry. Cost: starts at $56/vehicle; it’s more if you don’t have reservations, and there are additional fees for passengers.

From Bridgeport, it’s a 2-1/2-hour drive back to Boston, depending on traffic.

Kara Matuszewski Sassone is a former journalist who currently works in higher education. She’s the mother of 5-year-old twins – a boy and a girl – living outside Boston.

This writer received some complimentary stays, activities, and meals for the purpose of this review. However, all opinions expressed are solely her own.

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