Nestled around Fairmount Park and near both the Main Line and Philadelphia, Chestnut Hill is an idyllic year-round destination. Its walkable streets and historic architecture lend this town a feeling of Old World charm, but with all the perks of modern living. During the holidays—beginning before Thanksgiving—this bustling neighborhood dazzles with fairy lights and streets aglow with holiday cheer, making it the perfect destination for visitors from both far and near.

The festivities kick off on November 18, with the Circle of Trees at Woodmere Art Museum. Not only does the town alight with wreaths and swags, but the trees do, as well. Santa even swings by on an antique fire truck, taking a break from his North Pole duties. “We have the best time at Circle of Trees. It is such a fun way to kickoff the holiday season,” says Martha Sharkey, executive director of the Chestnut Hill Business District.

Woodmere’s holiday display remains throughout the season and other events, like Small Business Saturday and Morris Arboretum’s annual Holiday Garden Railway, are also big draws for families. “Trains chug along an outdoor quarter mile track. It’s a magical miniature village with thousands of twinkling lights around it,” says Sharkey of the railway display, noting it’s a huge draw for children.

There’s no shortage of options for families with little ones when wandering around Chestnut Hill. During the holidays, Sharkey recommends grabbing a sweet at Cake or Night Kitchen Bakery and Cafe, then heading to Woodmere’s straw bale maze and paying a visit to Santa and his elves for a photo. Sharkey also recommends Jenks Playground for little ones who have extra energy to burn.

While family fun abounds in Chestnut Hill, so does romance. For couples looking for a fun escape, Sharkey suggests making a weekend of it. “We have a wonderful hotel in our business district, the Chestnut Hill Hotel, which has 36 rooms. It’s a boutique hotel and it’s just beautiful. We also have Silverstone Bed & Breakfast located along Stenton Avenue,” says Sharkey. Visitors can spend the day shopping before grabbing dinner at one of the area’s many restaurants. “There is a great assortment of restaurants—Paris Bistro & Jazz Café, Chestnut Hill Brewing Company, which is our new beer garden, Mica which is a great BYOB for that romantic dinner, Tradewinds, Iron Hill Brewery, McNally’s Tavern and Tavern on the Hill—so there’s some kind of food for everyone.” To round out a romantic weekend, couples can take in some music at Paris Bistro or Woodmere, or catch a show at the semi-professional Stagecrafters Theatre.

Those who can’t make a weekend of it may want to visit Chestnut Hill for the famed Stag and Doe Nights. Stag and Does Nights have long been a tradition in Chestnut Hill, when the shops stay open late on selected Wednesdays throughout the season. This year, they will take place on Dec. 6, Dec. 13 and Dec. 20, allowing not only couples, but families to shop for loved ones. “It is our oldest and most favorite tradition,” Sharkey says. “All of our shops and restaurants have extended hours, we have a brass quartette and Santa swirling around the avenue—it’s a great night.” Those less inclined to go shopping can meander the antiques stores and art galleries like Isabella Sparrow, the Antique Gallery and the Philadelphia Print Shop.

Other holiday festivities include the Holiday House Tour, taking place December 9 this year, when visitors can get a glimpse inside some of the neighborhood’s lovely homes. This year, five homes bedecked in garland, wreaths and lights, will be highlighted. “You can truly get into the holiday spirit with this day spent touring several dramatic homes and you’ll get inspiration for your own home for the holidays,” says Sharkey. On December 16, the town comes alive with a holiday parade, which traverses Germantown Avenue, complete with a sighting of Santa. Kids line the streets in hopes of catching candy—and good favor with Old Saint Nick.

With all of the festivities, Chestnut Hill is a truly magical place to spend the holidays. “I like to walk the avenue and take in all that is around,” Sharkey says. “The shopkeepers know your name and can help you find that perfect gift for the person you’re shopping for during the holidays.”

Even after the holidays end, Chestnut Hill remains a wonderfully idyllic place to shop and dine with friends, spend the day with the family or enjoy a romantic weekend getaway. The holidays simply enhance the natural and historic charm, which is found few other places.

For more information on Chestnut Hill, its events, shops and more, visit www.chestnuthillpa.com.