Four distinct seasons and the perfect assortment of bustling cities and quaint coastal towns make New England a favourite travel destination all year long.

While the entire region is well-worth exploring (and you can drive south to north in a little over six hours), it’s the two most southern states of the region that have always had my attention; Connecticut and Rhode Island. Read on to learn what attractions are worth planning your trip around.

Connecticut

One of the original 13 colonies, Connecticut is known officially as the Constitution State, as it was home to (you guessed it), the United States’ first written constitution: the Fundamental Orders of Connecticut. Like much of New England, Connecticut is steeped in history and full of charm. Attractions here are so close, you can easily travel from coastline to countryside in a few hours.

TLW readers should note that Connecticut is home to more than 20 wineries spanning the whole state! While visiting them all would be an impossible feat in a day—or even a week—passports are given out along the Connecticut Wine Trail to keep track of the places you’ve visited, as well as to note your favourite wines from each vineyard.

New Haven

Start your trip in New Haven, Connecticut, easily accessible through nearby Bradley International Airport in Hartford.

New Haven is home to the prestigious Yale University. Current students lead free daily tours of one of America’s oldest universities. You’ll learn all about the rich 300-year history of the school, and have a chance to see inside Yale’s largest library, Sterling Memorial Library (featuring a coffered ceiling and stained glass galore), as well as the Beinecke Rare Book and Manuscript Library.

Top your visit off with a cocktail at Heirloom Bar, located inside The Study at Yale, a bespoke hotel located on campus.

Mystic

Be sure you don’t miss the waterfront town of Mystic, filled with 19th century architecture to admire, with 60 historic preserved buildings. The town was made famous by the movie, Mystic Pizza, where the eponymous restaurant has been serving up slices since 1973. All of the pies are made with a “secret recipe” sauce that has never been revealed. Be sure to stop by for a slice!

Mystic is also known for its marine trade legacy. The Mystic Seaport Museum is the nation’s leading (and largest) maritime museum and home to hundreds of shipbuilding tools, exhibits, and the recreation of a 19th-century seafaring village with trade shops and businesses from the 1800s that were transported to the museum from locations around New England.

Downtown Mystic features quaint buildings without a highrise in sight. The Mystic River Bascule Bridge, built in 1922, is open to both foot traffic and vehicles and allows boat traffic to travel through as well. It’s the most photographed bridge in Connecticut and a perfect spot for river views.

Washington

Also known as Washington Depot, this rural part of Connecticut is just 38 square miles and home to just 4,000 full-time residents. Washington is admired for its farmer’s market, farm-to-table restaurants, and beautiful inns, including the Mayflower Inn & Spa. This exquisite country retreat, nestled on 58 acres, was the inspiration for the popular television series Gilmore Girls, and the surrounding town looks just like a Hollywood set. The Inn is renowned as one of Northeast America’s most distinguished luxury hideaways, and is the perfect place to relax after a day spent exploring outdoor attractions like the Hollister House Garden, where you’ll find an 18th-century home situated on a sloping terraced site with English-inspired manicured country gardens, or Kent Falls State Park, a wonderland of waterfalls.

Rhode Island

Rhode Island. This isn’t just the smallest of the New England states — it’s the smallest state in America. Nicknamed “the Ocean State,” Rhode Island is known for its 400 miles of coastline, pristine beaches, Newport mansions, and Brown University.

Providence

Named one of the “10 Nicest Places in America” by Reader’s Digest, the capital city (the ‘Creative Capital’ to locals) of Providence is home to rich history, educational institutions, a vibrant arts scene and a diverse population.

One of the city’s most beloved ongoing events is WaterFire, an installation of more than 100 bonfires that burn bright in caldrons installed above the surface of three rivers that run through the city. The event unfolds multiple times throughout the year at nightfall, and nearly one million people experience it annually. Many attendees are students, as Providence is home to Brown University, the Rhode Island School of Design, Providence College, and five other institutions of higher learning.

Before leaving, be sure to walk Benefit Street’s Mile of History, lined with museums and preserved Colonial architecture.

Newport

An absolute must-visit in New England, Newport captures the hearts of visitors with its miles of craggy New England coastline, windswept beaches, and the nation’s largest collection of colonial era buildings.

Given Newport’s rich sailing history, one of the best ways to experience Newport is on the water, so consider taking a spin on a sightseeing cruise, where you can take in Newport Harbor and Narragansett Bay. Also accessible via ferry is Block Island is one of Rhode Island’s hidden gems; the Nature Conservancy called it one of the “12 Last Great Places in the Western Hemisphere.”

In downtown Newport you’ll find a mix of old and new, with cobblestone streets and old churches situated next to bars and nightlife. Stroll the harbor, home to hundreds of yachts from around the world, and dine at the nation’s oldest operating restaurant, The White Horse Tavern, open since 1673.

Newport’s most visited place is Cliff Walk, a free, 3.5 mile trail that traces the edge of the Atlantic Ocean and offers views of the manicured landscapes of the famed Newport Gilded Age mansions, including Breakers Mansion, built in 1895 by Cornelius Vanderbilt. There’s no wonder why it’s one of the most popular attractions in New England!

Stay nearby in the Chanler at Cliffwalk, a palatial romantic waterfront mansion completed in 1873. The Chanler at Cliff Walk blends the opulence of Newport’s Gilded Age (think chandeliers and fireplace) with the exquisite luxuries and amenities of today (like heated floors and oversized Jacuzzi tubs). Featuring just 20 beautiful guest rooms, the Chanler offers stunning ocean views, beautifully tended gardens, and luxurious in-room spa treatments. Dine at the hotel’s renowned five-star restaurant, Cara, which offers tasting menus featuring sustainable New England ingredients.