Road Tripping: The Best Routes from Boston, Massachusetts to Shelton, Connecticut

Heading out on a road trip is always an adventure – from finding the perfect playlist to mapping out your route. When traveling from Boston, Massachusetts to Shelton, Connecticut, there are plenty of options to consider that will get you to your destination in one piece and on time.

Route 1: The Fastest Way

If efficiency is your top priority, Route 1 is your go-to. Starting in Boston, follow the I-93 S towards Providence for approximately 35 miles until you reach the I-95 S. Take the I-95 S towards New Haven, and then continue onto the CT-34 W towards Derby/Shelton.

This route covers a distance of approximately 142 miles with a driving time of around two-and-a-half hours. But, since this is the most direct route, it can get congested at times, particularly during rush hour. There really isn't anywhere worth stopping but it's a speedy trip if you have an early morning meeting in Shelton.

Route 2: The Picturesque Route

If you're looking for scenic vistas and historic landmarks along the way, take a detour on Route 2. Starting from Boston, take the I-90 W towards Worcester, and then follow the I-84 W towards Hartford. Once you reach Hartford, take the CT-9 S towards Middletown, and then continue onto the CT-15 S until you reach Shelton.

This drive takes a bit longer than Route 1, covering approximately 166 miles with a driving time of around three hours. But, it takes you through stunning landscapes and historic towns like Sturbridge and Hartford. Be sure to stop at the Mark Twain House & Museum in Hartford for a leisurely afternoon, or grab a bite at The Glass Light in Sturbridge.

Route 3: The Coastal Route

If you prefer to stay along the coastline, opt for Route 3. Starting from Boston, take the I-93 S towards Quincy, and then head towards Weymouth and over to Fall River. From there, take the MA-24 towards Tiverton, Rhode Island, and then head north on the RI-114 towards Bristol. Continue north on the RI-114 to Pawtucket, cross the Seekonk River, and follow I-195 W to Shelton.

This route spans approximately 166 miles with a total driving time of around three hours. Along the way, you'll cruise through idyllic coastal towns like Newport, RI, with stunning views of the Atlantic Ocean. Make sure to stop and check out the Newport Mansions or grab a bite to eat at The Mooring.

Final Thoughts

When it comes to road tripping from Boston, Massachusetts to Shelton, Connecticut, the choice is yours. Each route offers a unique experience that will take you down different highways and byways, so ultimately it comes down to how much time you have and what kind of adventure you're looking for. But whether you're taking Route 1, 2, or 3, make sure to give yourself plenty of time to explore the sights and sounds along the way, and enjoy one of the most beautiful parts of the country.