Chestnut Hill's "Holidays on the Hill" Returns With Live Music, Parade Shopping Deals, and More - Wooder Ice
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Chestnut Hill’s “Holidays on the Hill” Returns With Live Music, Parade Shopping Deals, and More

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Chestnut Hill’s “Holidays on the Hill” Returns With Live Music, Parade Shopping Deals, and More

Chestnut Hill’s “Holidays on the Hill” Returns With Live Music, Parade Shopping Deals, and More

Chestnut Hill is once again transforming into a holiday wonderland. Beginning November 18 and running through December 25, Holidays on the Hill is back to offer visitors a chance to enjoy festive activations such   live sounds of a brass quartet, outdoor model train displays, shop during extended hours, and savor hearty holiday-themed food specials.

The Chestnut Hill Business District entices visitors with over 200 retailers, restaurants, and businesses to visit this season. Many are independently owned and feature uniquely handcrafted items by local artists. With a wide variety of shops, day-trippers can find the perfect holiday gift for anyone on their shopping list at multiple prices.

From shopping on Small Business Saturday to visiting the Holiday Garden Railway at Morris Arboretum to enjoying a beverage during the legendary Stag & Doe Nights, Chestnut Hill offers holiday experiences for all ages. Work up an appetite shopping? Many restaurants along the Avenue offer seasonal drink specials and savory dining options.

Holidays on the Hill Schedule of Events

Circle of Trees – November 18: A perennial favorite of local families and children, Chestnut Hill’s kick-off to the holiday season, Circle of Trees, returns November 18 from 5:30 to 7:30 p.m. Travel through Woodmere Art Museum’s (9201 Germantown Avenue) annual straw maze, enjoy hot chocolate, cider and cookies, and music provided by the Philadelphia Mummers. There will also be a visit from Santa, arriving on an antique fire truck.

Holiday Garden Railway – November 24 through December 30: Holiday Garden Railway at Morris Arboretum & Gardens (100 E. Northwestern Avenue) returns November 24 and continues daily from 10 a.m. to 4 p.m. through December 30. Visitors can view the enchanting rail cars and intricately decorated villages, which span over a third of a mile track surrounded by a festive wonderland of lights and sounds. Holiday Garden Railway is a marvelous
experience for visitors of all ages.

Small Business Saturday – November 25: Shop Chestnut Hill’s trendy and one-of-a-kind boutiques during Small Business Saturday and #KeepItOnTheHill. Check off gifts from your holiday wish list and support local retailers and restaurants throughout the day. From noon to 3 p.m., visitors can meet Santa as he strolls up and down Germantown Avenue and enjoy holiday tunes by a brass quartet.

Stag & Doe Nights – November 29, December 6, 13, 20: Chestnut Hill’s beloved annual Stag & Doe Nights return Wednesday during Holidays on the Hill from 5 to 9 p.m. Each night will feature unique entertainment, extended store hours, holiday specials, and complimentary refreshments and treats at many stores. Every Stag & Doe, from 6:30 to 8:30 p.m., shoppers can catch a glimpse of Santa strutting down the Avenue, greeting families while listening to the holiday sounds of a brass quartet.

Chestnut Hill Community Association Annual Holiday Parade – December 2 (rain date December 16): The Chestnut Hill Community Association Annual Holiday Parade takes place on December 2 at 9 a.m. at Chestnut Hill and Germantown Avenues. It finishes at 10 a.m. at Market at the Fareway (8221 Germantown Avenue). Entertainment includes the Phillie Phanatic, fire engines, marching bands, choirs, antique cars, horses, and participating local schools.

Chestnut Hill Community Association’s Holiday House Tour – December 9: Explore a curated selection of Chestnut Hill’s most stunning homes, each adorned with unique and festive decorations that capture the spirit of the season. Enjoy holiday music, treats, and special discounts at Chestnut Hill restaurants. Visitors can take advantage of free parking ALL DAY on Wednesdays from November 16 through December 24.

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