Old Saybrook to Portland train

Old Saybrook in Connecticut is a small but historic town along the end of the Connecticut River as it leads into the Long Island Sound. One of Old Saybrook's most famous residents was actress Katharine Hepburn, who lived here for much of her life. In the city, the Katharine Hepburn Cultural Arts Center, or The Kate, holds artifacts from her career and presents cultural events and performances for the community.

Old Saybrook is blessed with gorgeous waterfront settings for outdoor activities, including Harveys Beach on the Sound and an enormous wildlife refuge called The Preserve.

Amtrak Northeast Regional trains from Boston to New York stop in Old Saybrook daily. A local commuter line stops at the same train station and provides service to New London and New Haven, from where many other intercity train and bus routes depart.

Portland is Maine's largest city and, because of that, the main transportation hub in the state. From Portland, travelers can easily reach destinations such as Boston, Albany, and even Gainesville, Texas, by a combination of buses, trains, and ferries. And there’s plenty to do in the city, even if you’re traveling solo.

Since its foundation in 1786, Portland has recovered from no less than four major fires, creating a fascinating blend of old and new. The dedicated Arts District around upper Congress Street has a smattering of important museum collections, including the Portland Museum of Art, the state's oldest public art institution.

The West End hosts the majority of Portland's historic buildings, creating an olde worlde feel. However, the presence of several well-regarded schools and colleges ensures Portland remains one of the most vibrant small cities in the U.S.

After several years of hardship, the Old Port district has once again become the center of the action. Its attractive cobblestone streets and 19th-century red-brick warehouses now contain a selection of on-trend cafes, bars, and boutique stores. At the same time, it's still possible to watch the time-honored tradition of fishermen unloading their lobster pots onto the foreshore.

East of the downtown area, you'll find Munjoy Hill. It's a district with strong Irish and Italian roots, making it one of the best places in Portland to enjoy the authentic cuisine of Italy. It’s no wonder we named Portland one of our top vacation destinations in Maine.