The most wonderful time of the year is quickly approaching, and there's no place to spend the holidays quite like Chestnut Hill. The quaint neighborhood of Northwest Philadelphia transforms into a winter wonderland full of holiday festivities and seasonal cheer. Starting before Thanksgiving, these holiday events will keep the whole family entertained in the weeks leading up to Dec. 25.

Circle of Trees - Nov. 23

The free festivities begin at 5:30 p.m. at the Woodmere Art Museum. Guests can indulge in hot chocolate, cider and cookies while enjoying festive music. Kids will receive goodie bags and await Santa's grand entrance on an antique fire truck. Visitors can count down to the lighting of the art museum and surrounding trees. Attendees are encouraged to bring an unwrapped toy or new or gently used book to donate to a school-age child.

Holiday Garden Railway - Nov. 23-Dec. 30

Because of high demand, Morris Arboretum and Gardens is opening its Holiday Garden Railway one week earlier this year. Visitors can view the enchanting rail cars and intricately decorated villages spanning more than a third of a mile of track surrounded by lights and sounds. This exhibit is open daily from 10 a.m. to 4 p.m. Advance tickets are available for the Holiday Garden Railway: Nighttime Express on select nights, when the exhibit takes on a magical appearance in the dark.

Small Business Saturday - Nov. 30

Chestnut Hill is home to many trendy and one-of-a-kind boutiques and restaurants. During Small Business Saturday, support local retailers and #KeepItOnTheHill while checking gifts off your holiday wishlist. Santa will stroll Germantown Avenue from 1-3 p.m., and Christmas carolers in Victorian attire will sing classic holiday tunes, evoking the charm of a Dickens novel.

Stag and Doe Nights - Dec. 4, 11, 18

From 5-9 p.m. on Stag & Doe Nights, shoppers can enjoy entertainment, extended store hours, holiday specials and complimentary refreshments at many stores. From 6:30-8:30 p.m., Santa will stroll down the Avenue, greeting families while a brass quartet plays.

Arts & Eats First Friday - Dec. 6

Guests can stroll the cobblestone streets of Germantown Avenue during this monthly event. From 5-9 p.m., families and friends can explore Chestnut Hill's creativity, culture and cuisine. Holiday lights and decorations bring a Hallmark-like charm to the neighborhood. Kids can enjoy a special visit from Santa and hear festive melodies from a brass quartet between 6:30 and 8:30 p.m.

Chestnut Hill Community Association annual holiday parade - Dec. 7

The CHCA will host its annual holiday parade at 9 a.m. at Chestnut Hill and Germantown avenues. It ends at 10 a.m. at Market at the Fareway, 8221 Germantown Ave. The parade includes the Phillie Phanatic, fire engines, marching bands, choirs, antique cars, horses and participating local schools.

Chestnut Hill Community Association's holiday house tour - Dec. 14

The Holiday House Tour invites guests to explore select Chestnut Hill homes from 10 a.m. to 4 p.m. Each home will feature festive decorations capturing the season's spirit. Guests can enjoy live holiday music, treats and special discounts at local retailers and restaurants. Attendees can ride the event trolley between stops or visit at their own pace during the self-guided tour.

In addition to these holiday traditions and pop-ups, visitors can take advantage of free parking promotions starting on Nov. 29. The Chestnut Hill Parking Foundation will offer free parking in its six public lots every Wednesday, all day and all night, through Christmas.