Chestnut Hill’s Holidays on the Hill will kick off on Saturday, Nov. 17. The celebration, which runs through Jan. 6, spreads cheer throughout this holiday shopping destination, which is home to more than 125 independently-owned boutiques and restaurants. During Chestnut Hill’s oldest and most favored tradition, Stag and Doe Nights, festively decorated shops stay open late and welcome visitors with hot cocoa, wine tastings and seasonal treats on Wednesday nights, starting Nov. 28 and continuing through Dec. 19, while strolling carolers and brass quartets entertain shoppers along Germantown Avenue.

“With holiday charm and one-of- a-kind retailers on every corner, Chestnut Hill is a magical place to celebrate and shop this time of year,” said Philip Dawson, Executive Director of the Chestnut Hill Business District. “Visitors can find special gifts in our independent toy stores, galleries and clothing boutiques as they join in Holidays on the Hill festivities and make special memories with friends and family.”

The Holidays on the Hill merriment officially begins with the neighborhood tradition of the Circle of Trees lighting ceremony at Woodmere Art Museum on Nov. 17. Guests are invited to ring in the season with caroling, hot chocolate and cookies and the grand arrival of Santa Claus on a vintage fire truck. Attendees are encouraged to share the spirit of the holidays by bringing an unwrapped new toy to donate to the Chestnut Hill Hospital Toy Drive for a child in need.

American Express’s Small Business Saturday returns on Nov. 24, encouraging visitors to shop local and small in Chestnut Hill. The neighborhood’s cobblestoned main street, Germantown Avenue, features an array of trendy boutiques and specialty shops within walking distance, making it the perfect spot to kick off the holiday shopping season.

Families can spend Weekends with Santa throughout December. On Saturdays (Dec. 1, 8 and 15) Santa will make appearances at the Market at the Fareway (8221 Germantown Ave.) from noon to 3 p.m., and on Sundays (Dec. 2, 9 and 16) he can be found at Santa’s Headquarters at Laurel Hill Gardens (8125 Germantown Avenue) from noon to 3 pm. Kids can share their Christmas wishes and gather for memorable holiday photos with Santa and his elves.

Morris Arboretum brings back the beloved Holiday Garden Railway from Nov. 23 – Dec. 31 (closed Dec. 24 and 25). Model trains will chug along a quarter-mile track at the Arboretum surrounded by a miniature village adorned with thousands of lights in the winter garden. Guests can also bask in the evening glow of the decorated Arboretum during Holiday Garden Railway Nights on Dec. 1, 7, 8, 14, 15, 21 and 22.

Woodmere Art Museum recalls a cherished holiday classic in “The Night Before Christmas: The Illustrations of Charles Santore,” open Nov. 17 to Jan. 6.. In addition, the museum will exhibit 19th-century children’s toys, holiday trimmings and an extraordinary dollhouse replica of a Germantown rowhome decorated for the season.

On Dec. 8, the Chestnut Hill Community Association will host the 25th annual Chestnut Hill Holiday House Tour from 10 a.m. to 4 p.m. The ticketed tour invites guests to step inside five historic homes to enjoy holiday décor, seasonal treats and live musical performances. Attendees also receive discounts at restaurants and shops throughout Chestnut Hill.

The Chestnut Hill Community Holiday Parade brings holiday fun down Germantown Avenue for families to enjoy on Dec. 15. The parade, beginning at 9 a.m., winds its way through Chestnut Hill with local musical acts, floats, community groups and an anticipated appearance by Santa.