Road Trip

Road Trip

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Modern Montgomery

Antiques aren’t the only game in  town.
There’s  hip shops and eateries, historic buildings, and winter sports galore.

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by Lindsay Kennedy


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     Each September, the popular General Montgomery Day Festival draws huge crowds to the small town of Montgomery, nestled against the Wallkill River in northeastern Orange County. Twenty thousand partyers have been known to spill into the streets to watch the parades, shop for crafts, and cheer on local kids as they race in a soapbox derby. But excursions to Montgomery shouldn’t be limited to the fall months. The village’s charming, Mayberry-like center consists of several blocks around the intersection of Union and Clinton streets. With its surplus of historic architecture, colorful gift shops and antiques emporiums, the downtown is a perfect place to stroll at any time of the year. And in winter, a wealth of nearby outdoor activities (snowtubing anyone?)help keep the dark days’ blues at bay.

     Of course, Montgomery was put on the national map when the Orange County Choppers, those big, burly motorcycle makers whose shop is nearby, launched their own reality TV show on Bravo in 2002. But this sleepy town is experiencing all types of growth. On a recent weekend afternoon, as a crowd of teenage boys skateboarded down the sidewalks, longtime locals crowded into the Clinton Street Cafe to talk hunting, while shopkeepers debated whether the rumored arrival of more big-box stores not far from town will bring more business to village shops.

      Montgomery’s history begins with the area’s first settlers, a group of German Lutherans fleeing religious and political persecution who arrived in the 1700s. A Dutch settlement grew up north of the village, Scotch-Irish settled to the east, and the English put down roots farther north. In the 1730s, several of these settlers built the region’s first grist mill. A prominent citizen named James Ward bought the mill in the 1740s; he also built a wooden bridge by which farmers could bring their grains to the mill, hence the village’s original name, Ward’s Bridge. The bridge has been replaced three times; the current span, illuminated every evening by charming white lights, still brings commerce back and forth.

      The village retained its identity as Ward’s Bridge until the end of the Revolutionary War, when its name was changed to honor Gen. Richard Montgomery, a Continental Army soldier killed on New Year’s Eve 1775 while attempting to wrest the city of Quebec from British control. The Montgomery Academy,  incorporated in 1791, served as both a grammar and high school throughout the 19th century. Today, the academy’s historic brick building serves as the Village Hall; its library is open for regularly scheduled hours, and a small historical museum can be toured by appointment. Jacob Tooker, an academy headmaster, lived across the street in what is now the Mead-Tooker House, an eight-bedroom bed-and-breakfast listed on the National Register of Historic Places. Those looking to unwind after the busy holiday season can select the B&B’s “Tranquil Indulgence” package, which includes a two-night stay and a one-hour therapeutic massage session in your room.


     In Montgomery, winter does not mean you must stay indoors. The Thomas Bull Memorial Park, on Route 416, and Winding Hills Park, located on Route 17K, offer a variety of winter sports. The highlight? Snow tubing! In winter, the Thomas Bull’s Stony Ford golf course driving range turns into a slider’s paradise: kids (and plenty of adults) glide down an 800-foot hill on specially designed snow inner tubes (they have plastic bottoms for extra speed). For $10, you can rent a tube for one of four 90-minute sessions offered every weekend and on school holidays; two additional sessions run on Friday and Saturday nights. For those who prefer to descend their hills in a more traditional fashion, sledding is also popular here. In addition, a pond and artificial skating rink are available for recreational skaters, and the golf course transforms itself into a cross-country skiing trail. At Winding Hills, 40-acre Diamond Lake is a hot spot for ice fishing, and hiking trails are open for snowshoeing and cross-country skiing. If that isn’t enough, snowmobiles are also permitted (after being registered at the Park Ranger’s office).

After hanging up their skates and skis, visitors can trek into the village for some of the most unique shopping around. Montgomery is something of a mecca for antiques- and Americana-hunters. At the Clinton Shops, on

Clinton Street

, a dozen dealers display their various and ever-changing wares. Coal-Bin Antiques is a must for those interested in antique toys, vintage posters and tin advertising signs. Specializing in French enamelware, Blue Shutter Antiques  is housed in the original kitchen of the Borland House, a Greek Revival-style bed-and-breakfast operated by Carol and Bill Freeman. (Aspiring innkeepers can spend January 19-21 learning the tricks of the trade from the Freemans, who are hosting a seminar on the ins and outs of running your own B&B.)

      Swing by Maple Hill Gifts on

Union Street

for custom-made, handcrafted furniture; also be sure to browse the wide selection of gifts and Eastern European objects on display (I liked the pretty Russian nesting dolls). Make your way next door to Fancy That for some early Valentine’s Day shopping. A village fixture for the past 17 years, the store specializes in antique and vintage-looking jewelry. Handmade jewelry as well as chic handbags and diaper bags (designed by Lori Buckley, who also sells her wares at Bloomingdale’s) can also be found at the Jezebelle Gift Boutique. Brides-to-be can head over to Reginella, an old-fashioned

Union Street

bridal salon offering everything from dresses to invitations — and personal service by owner Rita Alaimo.  Clothes horses will want to visit Christine’s Closet on

Clinton Street

. Operating until recently as the New To You consignment shop, Christine’s Closet bills itself as a “chic, cheap boutique” that stocks popular labels like Ann Taylor, Banana Republic, and Coach. The store is also the home of the Gowns to Girls program, a not-for-profit organization that provides special occasion dresses to girls from  low-income families.

      For a relaxing shopping experience, head over to La Befana’s Specialty Gift Shoppe on Union Street, where owner Laura Colavito-Agosta stocks soothing therapeutic essential oils, some homemade, at this New Age-meets-Victorian-era store. Nearby, Tomorrow Morning, a diminutive spot at the crossroads of Union and Route 17K, offers inspirational gift items. And no trip to Montgomery would be complete without a visit to the Village Sampler: this

Clinton Street

staple takes you back to the days of yore with two floors crammed with whimsical gifts, Crabtree and Evelyn bath products, and a large selection of to-die-for chocolates.

      Enjoy a cappuccino, a personal pot of tea, or a delectable sandwich at  the Daily Bean Café, an inviting

Union Street

lunch spot, where paintings by local artists grace the walls. Nearby  are family-friendly restaurants Fab III and Village Pizza. Those in the mood for Italian food must visit La Mia Cucina Focacceria Ristorante. The husband-and-wife team of Tom and Joanna O’Connor opened the place last fall, and have been serving up a traditional menu worthy of Manhattan’s Little Italy. A block away sits Pazzo Italian Grill, whose charming stone fireplace is an ideal spot to enjoy their popular eggplant rollatini. Across the street is the Zagat-rated Wildfire Grill, where chef Krista Wild offers an ever-changing menu that includes ostrich and New Zealand lamb in an African-inspired setting. Those in a more casual mood hang out at Copperfield’s, a Clinton Street restaurant and bar, while anyone hankering for comfort food must try the pot roast at Camillo’s at the Crossroads, located at the junction of Routes 17K and 208.

     In the mood for romance? Try

88 Charles Street

Café, which features Northern Italian and Continental cuisine in an elegant atmosphere, with live piano music on Friday and Saturday nights. And the Ward’s Bridge Inn, housed in a historic building opposite the Montgomery firehouse, has a graceful dining room and world-class food.

     So get going. Whether your inclination is to sled, shop or restaurant-hop, Montgomery offers something for everyone this season.

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