Lenox, Massachusetts named Best Northeastern Small Town

New Hope, Pennsylvania takes second place

When you think of a quintessential American small town, the charming hamlets of New England likely come to mind. The Northeastern United States – Connecticut, Delaware, Maine, Maryland, Massachusetts, New Hampshire, New Jersey, New York, Pennsylvania, Rhode Island and Vermont – are brimming with travel-worthy small towns.

  • Lenox

    At the heart of the Berkshires lies the village of Lenox, home of the famous Tanglewood Music Festival and a popular summer getaway. The core of the town features several shops and eateries, all surrounded by some mighty impressive homes. Visitors to the Ventfort Hall Museum have the chance to see inside one of these Gilded Age homes.
    Photo courtesy of Massachusetts Office of Travel & Tourism

  • New Hope

    A short drive from Philadelphia sits the town of New Hope, connected by a footbridge to the town of Lambertville on the other side of the Pennsylvania/New Jersey border. This town on the Delaware River is known for its antiques dealers, art galleries and restaurants. The towpath along the Delaware Canal makes for pleasant stroll or bike ride through the Bucks County scenery.
    Photo courtesy of Harvey Barrison / Flickr

  • Clinton
    New Jersey

    Scenic Clinton straddles the Raritan River, its two halves joined by a 19th century iron bridge connecting a pair of historic gristmills. The bridge offers stellar views of the town's 200-foot-wide waterfall, and the two mills now house Red Mill Museum Village and the Hunterdon Art Museum. Cafes, galleries and specialty shops line Clinton's Main Street.
    Photo courtesy of Thinkstock

  • Woodstock

    Woodstock's exquisite downtown area features numerous galleries and boutiques, while the surrounding historic homes are a study in 19th and 20th century architecture. Settled in 1765 on the banks of the Ottaquechee River, Woodstock has become a four seasons destination for shoppers, foodies, antiquers, outdoor enthusiasts and history buffs alike.
    Photo courtesy of Woodstock Chamber of Commerce

  • Essex

    Surrounded on three sides by water, the historic small town of Essex oozes New England charm. One of the town's most popular attractions in the Connecticut River Museum, housed within a 19th century warehouse. Shops, restaurants and Colonial and Federal-style homes line the Main Street, where visitors can stay at an inn that has been welcoming travelers since 1776.
    Photo courtesy of Juliane Schultz / Flickr

  • Cape May
    New Jersey

    A Victorian gem on the New Jersey seashore, Cape May is one of the oldest resort towns in the country. The entire city is a National Historic District with some 600 preserved 19th century buildings. Colorful gingerbread buildings, excellent birdwatching opportunities and a relaxed vibe make this a favorite escape, even today.
    Photo courtesy of Thinkstock

  • Rockport

    Located 40 miles northeast of Boston on the tip of Cape Ann, the tiny town of Rockport has been around since 1690 as a bustling fishing port and a popular summer resort community. Motif No. 1, a wooden fish warehouse in the Rockport wharf is the town's most recognizable landmark, but visitors can also enjoy art galleries, shops, a house made from newspapers and the natural beauty of nearby Halibut Point State Park.
    Photo courtesy of Tim Grafft/MOTT

  • Eastport

    The town of Eastport, situated on the easternmost coast of Maine, was once a major center for the sardine canning industry. Lately, the town has reinvented itself through a revitalization of its four block downtown.The town's most noticeable attraction is a giant statue of a fisherman, the remnant of a Fox television show filmed in Eastport in 2001, but visitors can also hike Shackford Head State Park, tour Raye's Mustard Mill, or board a windjammer for a whale watching or sunset cruise.
    Photo courtesy of Kim Carpenter / Flickr

  • Bar Harbor

    It's hard to deny Bar Harbor's charms, from its National Historic District along West Street to its collection of B&Bs, cafes and ice cream shops. This gateway to Acadia National Park on Mount Desert Island has been one of Maine's top summer resort towns since the 19th century; several of its lavish mansions remain.
    Photo courtesy of AppalachianViews / Thinkstock

  • Meredith
    New Hampshire

    A mountain town on the shores of Lake Winnipesaukee, Meredith features several historic sites, as well as specialty shops, restaurants and the chance to ride the Winnipesaukee Scenic Railroad. Walking paths wind along the banks of the lake, while Mills Falls Marketplace offers distinctive shopping on the grounds of a former linen mill.
    Photo courtesy of Thinkstock

In fact, when we asked a panel of local experts to nominate their favorites (each with a population of under 10,000 according to the latest census data), the 10Best editorial team found ourselves with more than 80 to choose from. After narrowing it down to 20 nominees, we turned the list over to our readers to help choose a winner. The results are in!

The top 10 winners in the category Best Northeastern Small Town are as follows:

  1. Lenox, Mass.
  2. New Hope, Penn.
  3. Clinton, N.J.
  4. Woodstock, Vt.
  5. Essex, Conn.
  6. Cape May, N.J.
  7. Rockport, Mass.
  8. Eastport, Maine
  9. Bar Harbor, Maine
  10. Meredith, N.H.

A panel of experts partnered with 10Best editors to picked the initial 20 nominees, and the top 10 winners were determined by popular vote. Experts Deborah Fallows (American Futures), Anna Hider (Roadtrippers), Jenna Intersimone (MyCentralJersey.com) and our team of 10Best Local Experts were chosen based on their knowledge and experience of Northeastern travel.

Other nominated towns included Berlin, Md.; Block Island, R.I.; Camden, Maine; Chester, Vt.; Cold Spring, N.Y.; Jim Thorpe, Penn.; Lewes, Del.; Milton, Del.; Oak Bluffs, Mass.; and Washington, Conn.

Congratulations to all our winning small towns!

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Deborah Fallows

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