Cross Two States in a Single Hike on This Epic Massachusetts Trail

Most, if not all, of us have crossed state lines in our cars, or perhaps on public transportation. Am I right? But have you done it on foot or by bike? If that sounds like your kind of adventure, then I’ve found the perfect day hike for you. Imagine hiking past sprawling fields, scenic waterways, and over footbridges, through old railroad tunnels, as the crisp morning air fills your lungs. And if that wasn’t enough, in less than 5 miles, you’ll end up in Connecticut. 

You can have that and more when you hike (or bike) the Southwick Rail Trail near Westfield. Since you can hike two states at once in Massachusetts and Connecticut, this is by far one of the coolest hiking experiences in the area. Are you ready to take on one of the most scenic cross-state hiking trails in New England? Let’s go!

Trail Overview: Distance, Difficulty, and Scenic Highlights

If you guessed that the Southwick Rail Trail was once a railroad, you would be correct. It was part of the New York/New Haven/Hartford Railroad, which was transformed into a network of urban rail trails extending all the way to New Haven, CT. The 7-mile point-to-point trail begins near the Westfield/Southwick town line. It connects to the Columbia Greenway Trail in Westfield, so you have the option of extending the route by starting there. The pathway is fully paved, making this an easy, family-friendly hike everyone can enjoy. Expect to see bikers, joggers, moms with strollers, wheelchair users, and dogs as you hike.

The scenery along the way is the highlight of this urban trail. As it meanders through the serene countryside, you’ll pass historic farms, expansive fields, wetlands, and flowing streams and waterways. The kids will love the whimsical tunnel painted with large, colorful sea creatures. Also, Congamond Lakes is accessible from the trail. Once you get to the Connecticut border, you’ll glimpse what’s left of the historic New Haven to Northampton Canal. After crossing the state line, the path seamlessly connects to the Farmington Canal Heritage Trail near Granby and Suffield, CT.

At this point, you can continue your hike or ride into Connecticut and spend some time checking out the nearby towns. My favorite part? Although this is an urban trail, there are scenic sections that make you feel like you’re miles away from everything. It is those quieter spaces where you can breathe and really enjoy the peaceful countryside. This trek across the state line is easily one of the best hiking trails in Massachusetts.

Nearby Attractions and Local Stops to Extend Your Adventure

The beauty of this urban trail is that you’ll have access to the attractions in not one, not two, not three, but four towns, especially if you're on a bike. This means you’ll have plenty of opportunities to extend your day. My recommendations? If you start your hike in the morning, grab coffee or a hearty, protein-packed sandwich at Congamond Coffee & Cafe. The coffee shop is just a short two-minute walk from the trailhead parking lot. You can also grab something hearty at Rail Trail Ale House, located directly on the trail.

Since the path meanders by Congamond Lakes, bring your rod and catch largemouth bass, bluegill, and sunfish. Or if you prefer to skip the water, pack a lunch and have a picnic as you watch the ducks splash and play. Or simply sit back and soak up the shimmering water views. You can't go wrong no matter what you choose to do.

Want to really extend your adventure? On the Connecticut side, you can explore both Granby and Suffield as you hike/ride along the Farmington Canal Heritage Trail. Here, you'll find rural farmlands, farmhouses, breweries, historical sites, and more. If you’re on a bike, I'd suggest riding through the towns, creating your own unique adventure on this cross-state hiking trail through Massachusetts and Connecticut. For hikers, you can soak up the peaceful scenes in rural Suffield on this day hike. Grandy would add a few extra miles to your adventure, but if you have extra time, go for it!

After you get back to the trailhead, make your way to Westfield and treat yourself to the kielbasa Snack at Janik’s Pierogi Cafe, an authentic Polish restaurant. You can thank me later. Be sure to carve out time to see Westfield River Esplanade; the views of the river are breathtaking.

Best Time to Hike This Massachusetts Trail for Weather and Views

The trail comes alive in the fall when the trees blaze with autumn beauty. In spring and summer, expect lush green meadows and flowing streams. The area transforms into a winter wonderland in the frosty season. To be honest, no matter when you visit, the hike will be very rewarding, each season bringing its own character. Of course, when the weather is pleasant in the spring, summer, and fall, expect the trail to be crowded. No matter when you visit, you will be delighted by all that this trail has to offer. 

Have you ever hiked through two states in one day? Or have you hiked the Southwick Rail Trail or any of the other trails in the network? If so, what are some of your favorite stops along the way? Tell us on our nomination page. And if you’re searching for another bucket-list-worthy adventure in the area, check out the Connecticut River Loop. Along the way, you can explore multiple state parks, featuring historical sites, peaceful waterways, and sprawling mountain views. 

Or when you’re feeling inspired, use Only In Your State’s itinerary planner to discover more unique hiking trails in the New England area.