New England Fall Road Trip: Coastlines, Foliage and Best Western

Our October New England trip included Portland Head Light, Crawford Notch, Beavertail State Park, Wadsworth Falls and East Rock Park. This overview brings those stops together with our hotel stay in Vermont.

Sponsored by Best Western.

We flew into Boston on a red-eye and built our October New England trip around fall color, photography, disc golf and time along the coast. The route took us through Massachusetts and New Hampshire to Maine, back through the mountains into Vermont, then south to Connecticut and Rhode Island before returning to Massachusetts. We moved hotels most nights, with two nights in Waterbury giving us a little more time around Stowe.

Some of my favorite moments were the ones we stayed for: moonrise off the Maine coast, still-water reflections in Crawford Notch and sunset at Beavertail. A storm changed our plans near the end, too. This is how our trip unfolded, with the individual guides linked below for practical details.

Starting in Massachusetts and New Hampshire

We began with disc golf in Massachusetts after the overnight flight, then headed to our New Hampshire hotel for a much-needed nap. That evening we walked across the parking lot to Backyard Brewery for dinner. The food, flight and live band made it one of our favorite stops, enough that we drove back for another visit later in the trip.

Maine: Portland Head Light and the coast

The next day took us to Maine and Portland Head Light. One of my favorite photographs came from watching the moon rise over Ram Island Ledge Light offshore. We also spent time in Portland before staying overnight in Maine.

Check park hours, parking and museum details before visiting.

New Hampshire: autumn in Crawford Notch

From Maine we drove back into New Hampshire's mountains, stopping often for photographs. At Willey House Historic Site, we arrived around sunset, took a short walk and worked with the mountain reflections in the still water. It became one of my favorite areas of the trip. We reached Vermont late that night.

Crawford Notch State Park has more options if you want to spend longer in the mountains. Choose a walk that suits your group and leave time to learn about the site’s history.

Connecticut and Rhode Island

After Vermont and another night in Massachusetts, we continued into Connecticut. We caught a break in the rain for Wadsworth Falls, where the water was powerful and we took long exposures. East Rock Park was a shorter photo stop, parking near the overlook and walking out for the view. We also visited Lighthouse Point Park. Seeing how the fall color changed as we traveled south was a big part of the drive.

After a night in Connecticut, we headed toward Rhode Island along I-95. In Newport we drove past estates including Rosecliff, Beechwood and Marble House, seeing them from outside rather than taking interior tours. Our ocean exploring and sunset photographs were at Beavertail State Park in Jamestown, before another overnight stay in Rhode Island.

Use the individual guides to plan access and walks at each place.

More ideas: Boston and Woodstock

If you want to add other stops, Boston offers history, neighborhoods and a change from the outdoor scenery. The National Park Service’s Boston guide introduces the Freedom Trail and Black Heritage Trail.

For more time in Vermont, you could add Woodstock to your route.

Where we stayed: Best Western Plus Waterbury - Stowe

We spent two nights at Best Western Plus Waterbury - Stowe in Vermont. It was the only hotel where we stayed two nights on this trip, giving us a full day in the area instead of immediately packing up again.

If you are planning a stay in the area, the hotel’s official page has room details and availability. For other overnight stops, browse Best Western’s New England hotels.

Choose your hotels around the places you want to spend time. Staying in more than one area can save you from retracing the same roads each day.

Spending more time around Waterbury and Stowe

If you build a Vermont day around your hotel stay, Route 100 between Waterbury and Stowe is part of the Green Mountain Byway. It gives you a route between the two towns rather than a separate drive to add to an already full day.

We loved stopping at Cold Hollow Cider on Waterbury-Stowe Road and walking around historic Stowe village. We also had dinner in town, and I would highly recommend spending some time here if you can extend your stay. For more places to explore while you’re in the area, take a look at Stowe’s fall trip ideas.

We also stopped at Ben & Jerry's for ice cream and explored the grounds and flavor graveyard. We did not take the factory tour. Between those stops, disc golf and walks through the fall scenery, the extra night in Vermont made sense for us.

A storm changed our Massachusetts plans

We had planned to stay closer to the Massachusetts coast after Rhode Island, but a storm knocked out power at our intended accommodation and we were rebooked. We ended up spending time in Salem instead. October crowds were huge, and walking around gave us a very different experience from the quieter parks earlier in the trip.

One evening, back at our Massachusetts hotel and thinking about dinner, we decided we liked Backyard Brewery enough to drive back into New Hampshire for it. The following day we headed into Boston for our flight home. The route was not a perfectly tidy loop, but the mix of mountain stops, coastal evenings and places we wanted to revisit is what I remember most.