Oakmont’s holiday events (kicking off this weekend) are straight out of a Christmas movie

Oakmont sparkles at the holidays. Photo above by Bharat Mankani.

Nestled along the Allegheny River, Oakmont transforms into a cozy, twinkle-lit wonderland during the holiday season. This small town knows how to do the holidays right — think Victorian charm meets modern-day cheer. You’ll find cobblestone streets alive with carolers, the scent of pine and freshly baked cookies wafting through the air, and storefronts decked out in their holiday best. 

Whether you’re wandering through candlelit tours of the historic Kerr Museum or grabbing hot cocoa during the Hometown Christmas Parade, Oakmont offers an irresistible mix of nostalgia and merriment.

Here are the must-attend festivities:

EVENTS

The big Hometown Christmas & Parade
Saturday, Nov. 23, 3 p.m., Allegheny River Blvd

Get ready to jingle all the way down Allegheny River Boulevard at Oakmont’s Hometown Christmas & Parade! The festivities kick off with food, drinks, trolley rides, shopping, a 42-unit parade and even a dazzling drone show. Oh, and of course, Santa himself! This is your one-stop shop to get into the holiday spirit while tackling your gift list. Did we mention you can ride a trolley to Santa’s favorite cookie stop? Now that’s holiday cheer.

A decked-out Christmas Home Tour
Sunday, Dec. 1, noon to 5 p.m.

Nothing says “holiday spirit” like a tour of the most beautifully decorated homes in Oakmont. Take a self-guided tour of local homes decked out in their holiday best. After the tour, head to Amanda Lee Glassware for the Christmas Market. (Who doesn’t love a little shopping after a holiday tour?) Tickets are $25 in advance, a nice gift for holiday lovers.

A very merry Carol Walk
Sunday, Dec. 8, 6 p.m., 378 Delaware Ave, Oakmont

Sing your heart out with the Oakmont community during this beloved holiday tradition. Join the Annual Christmas Carol Walk, starting at St. Thomas Episcopal Church, and meander your way along the streets, caroling with fellow festive spirits at each stop. You’ll be serenaded by joyful choirs from St. Irenaeus Catholic Church to Oakmont Methodist and Oakmont Presbyterian Church. The grand finale? A big group sing-along is followed by refreshments and plenty of community spirit.

Victorian splendor at the Kerr Museum
402 Delaware Ave, Oakmont, various dates through Jan. 4 (see below)

Experience the warmth and charm of life as it was lived by a small-town doctor. Dr. Thomas R. Kerr, his wife Jessie, and daughter Virginia lived in their gracious home in Oakmont, which provided an escape from the often harsh conditions of life in the city. The museum portrays middle-class family life in the late 19th century. This period was marked by the extremes of fabulous wealth and grinding poverty, which overshadowed the emerging middle class. Here are their holiday exhibits: 

A Visit from Santa Claus at Kerr Museum
Nov. 8 through Jan. 4, by appointment
The Kerr elves are planning daytime tours for their guests, and this year’s tour will feature Santa Claus. The museum will highlight how Santa Claus became an important facet of holiday life. Click here for details on tours or call 412-826-9295. 

Christmas Candlelight Tours of Kerr Museum
Friday, Dec. 6 and Friday, Dec. 13, 5:30 p.m., 6:30 p.m., and 7:30 p.m.
Call 412-826-9295 to book a daytime Christmas exhibit tour or a special Christmas Candlelight tour. Advanced pre-paid reservations are required. 

Last Call Cookie Crawl
Saturday, Dec. 21, 2024, 10:00 a.m. – 4 p.m., Allegheny River Blvd

It’s the most delicious time of the year. Get ready for one last festive stroll. Your cookie-filled adventure supports the Dolly Parton Imagination Library, promoting children’s literacy. It’s sweet, it’s local, and it’s for a good cause.

FOOD AND DRINK 

Indulge at Oakmont Bakery, 1 Sweet St, Oakmont

If there’s one place that captures the magic of the season, it’s Oakmont Bakery — a local landmark where you’ll feel like a kid in a candy store (or, more fittingly, a bakery!) From Santa-themed cakes to decadent Yule Logs, families and friends can come together to pick out their seasonal must-haves. 

Also, GingerBell Rock returns for its sixth year, as Inner Groove Brewing teams up with Oakmont Bakery for this holiday favorite. On Saturday, Nov. 30, from 12–4 p.m., guests can enjoy pints of the gingerbread cookie brown ale paired with fresh bakery cookies at a special pop-up bar inside Oakmont Bakery.

Celebrate the Season at Acclamation Brewing, 314 Arch St, Verona

This December, Acclamation Brewing (in Oakmont’s twin borough of Verona) offers holiday fun, creativity, and good cheer.

• Kid’s Cookie Decorating Class: Saturday, Dec. 7, 11:30 a.m. – 1 p.m. Kids can learn the basics of cookie decorating in this beginner decorating class. Ticket includes all supplies, cookies and instruction, with the option to make it a parent/kid combo. 
• Dog Photos with Mr. and Mrs. Claus: Saturday, Dec. 7, 2 p.m. – 5 p.m. Dogs deserve to tell Santa what they want for Christmas, too. Come out and meet Mr. & Mrs. Claus and get a free photo from Jessica Lynn Photography. Donations will be collected for 412 Animal Rescue of Verona. 
• Grown-ups Cookie Decorating Workshop: Dec. 12, 6:30 p.m. – 8 p.m. Get into the festive spirit with Pittsburgh Cookie Table, featuring supplies to craft an adorable nativity scene, plus a drink on the house!
• Candles & Cheers: Thursday, Dec. 19, 6:30 p.m., You can create custom-scented candles by Oakmont Candle Works while enjoying Acclamation’s brews. Watch their Facebook page for an event post to get tickets.

Get festive at The Oaks Theater, 310 Allegheny River Blvd, Oakmont

Get into the holiday spirit at The Oaks Theater, where the magic of Christmas comes alive with two events this December:

• Sounds of Christmas: Sunday, Dec. 8, 3:30 p.m. Featuring the Latshaw Pops Orchestra, dazzling costumes, joyful carols, and a visit from Santa Claus. Tickets are $40. Doors open at 2:30 p.m.

• A Christmas Music Spectacular: Thursday, Dec. 19, 7:30 p.m. Hosted by KDKA’s Larry Richert, featuring performances by The Nied’s Hotel Band and guest musicians. Table seating for four is $140; individual theater seating is $25. Doors open at 6:30 p.m. A portion of proceeds benefits the Greater Pittsburgh Community Food Bank.

Be Creative at the Oakmont Carnegie Library
Saturday, Dec. 7, noon – 1:30 p.m., 700 Allegheny River Blvd

Get into the holiday spirit with a fun and creative workshop at Oakmont Carnegie Library. Participants will create custom holiday cards, gift tags, mugs, or tote bags using Cricut machines. Materials include iron-on vinyl, permanent vinyl, and card stock, perfect for personalized gifts or decorations. Registration deadline: Dec. 1.