5 Day Trip Date Ideas for Boston

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Everyone needs to escape the city sometimes, especially now that the hordes of college students are back in town and taking over Boston. Get some respite when you fit these five day trip dates into the final days of summer and explore all that New England has to offer, without even renting a Zipcar. Nowhere else in America can you cross state borders so quickly and conveniently.

Portsmouth, NH

There’s plenty to do in Portsmouth—the nation’s third-oldest town with a live history museum to prove it—and the best part is you can explore it all by foot. Pop into shops of all kinds ranging from bookstores, antiques and boutiques, sit aboard a harbor cruise and indulge in fresh seafood on the waterfront. Top the trip off with some craft beer from Portsmouth Brewery (New Hampshire’s first brew pub), or their sister company Smuttynose.

Get there: Ride C&J Trailways bus service from South Station to Portsmouth.
Est. Time: 1 hour and 40 minutes.


Portland, MA

Growing greenEscape the land of tall buildings and corporations to Portland, a foodies promised land where everything is hyper-local, eco-friendly, recycled and farm-raised. Shop made-in-Maine arts and goods, stop in at Maine Meade Works (fermented honey) or the Urban Farm Fermentory for an experience you definitely can’t get in Boston. Then take the Ferry to Peaks Island for a cruise along the coast and don’t—seriously don’t—leave before gorging on some lobster.

Get there: Take the Amtrak Downeaster from Back Bay to Portland.
Est. Time: 2.5 hours.

Salem, MA

175663Halloween comes early when you head to Salem. Check out all of the history dating back to the 1692 Salem Witch Trials as you stroll the narrow streets of this quirky, and don’t forget haunted, seaside town. Stay after nightfall and go on a ghost hunt—the perfect excuse to hold your date’s hand.

Get there: Take the Salem Ferry from Boston’s Long Wharf or the Commuter Rail.
Est. Time: Under an hour.

Beach Day

CapeFlyer-660x439Get one last beach day—or weekend— in before the seasons change and you’re not able to bare skin for another eight months or so. And don’t worry, you don’t have to settle for Revere, as there are better stretches of beach within reach by commuter rail. Consider Maine’s Old Orchard Beach, Easton Beach in Newport, RI (with a 3.5-mile cliff walk) or hop on the new CapeFLYER for a weekend at the Cape with access to both Nantucket and Martha’s Vineyard by ferry.

Whale Watching in Gloucester, MA

The Cape Anne coastline in Gloucester is home to the Top 10 places for whale watching in the world, and the No. 1 in MA. It’s a unique experience to get up close and personal with the gentle giants of the sea—and they’re pretty much guaranteed to jump in the air right in front of you Shark Week-style. Before heading home walk through the historic downtown and stop in for some grub and live music on the waterfront.

Get there: Take the Newbury/Rockport Commuter Rail line to Gloucester. Then board the trolley shuttle.
Est. Time: 1 hour.


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