Weekend Getaways: An extensive 3-day itinerary to Chestnut Hill, Pennsylvania

Take a drive to this quaint Philadelphia suburb for a romantic getaway this fall.

tourists in Chestnut Hill
Photo courtesy of Visit Philadelphia

Drive time from NoVA: 2 hours 45 minutes

Known as Philadelphia’s Garden District, this historic suburb (it used to serve as a summer playground for Philly’s wealthy in the 1700s) of cobblestone streets, offers a romantic, walkable getaway with an abundance of arts and culture, two notable arboretums and a variety of dining options. This romantic destination incorporates culture, history and playful exploration. Chestnut Hill will inspire couples to bond over effortless travel and revel in new discoveries.

Where to Stay

The town’s preeminent lodging is the Chestnut Hill Hotel. Designed using Wissahickon stone, the 36-room boutique hotel was constructed in 1894. During Prohibition, the place was transformed into a speakeasy and brothel, but after its notorious saga, has become a luxury hotel that blends traditional architecture with modern conveniences. There’s also Silverstone Bed & Breakfast in a Victorian-Gothic home filled with well-appointed guest rooms, a lovely patio and full breakfast. Just a few miles away is the Chubb Hotel & Conference Center. Surrounded by knolls and wooded grounds, this contemporary hotel offers suites, and Chubb’s dining is overseen by Philadelphia’s acclaimed chef Jose Garces.

morris arboretum
Photo courtesy of Morris Arboretum

Day 1

Morning
Start your day at Chestnut Hill Coffee Co., an upscale espresso bar, which roasts beans in-house, and then move onto the cultural attractions and gardens that gave rise to the neighborhood’s reputation. The 92-acre Morris Arboretum attracts garden enthusiasts from around the world who come to revel in the intense hues of native maples, dogwoods and oaks, and to enjoy special pieces like Patrick Dougherty’s new Stickwork sculpture.

Afternoon
McNally’s Tavern is your go-to lunch spot for Philly cheesesteaks or the Schmitter, a sandwich adorned with salami, steak, fried onions and signature sauce. McNally’s iconic sandwiches have been a local favorite since 1921. Post-lunch, head to the Woodmere Art Museum. The museum’s holdings include more than 8,000 thought-provoking paintings and sculptures by celebrated, local artists like Harry Bertoia, Benjamin West and Violet Oakley.

Evening
For dinner, reserve a table at Chestnut Hill’s Paris Bistro & Jazz Cafe. You’ll feel you’ve entered the Gilded Age, thanks to the Parisian decor and improvised tones by Philly’s finest jazz musicians. The menu features quintessential French cuisine like steak frites and escargot.

new stick scultpure
Photo courtesy of Morris Arboretum

What’s New

The new Stickwork sculpture, Loop de Loop, by artist Patrick Dougherty, is like a hide-and-seek game structured with a maze of loops and tunnels. This new installation is one of three by Dougherty that has been displayed at Morris Arboretum. Using woven, repurposed willow sticks and saplings, the outdoor sculpture helps visitors become one with nature.

cliveden of the national trust
Photo courtesy of Visit Philadelphia

Day 2

Morning
Head to neighboring Germantown, where homes date back to the Revolutionary War. Begin at Cliveden of the National Trust, which in 1777, housed British troops during the Battle of Germantown. After the battle, Cliveden’s owners sold the property and it was used as a summer home, and tours at Cliveden focus on stories of privilege and oppression.

wyck historic house and garden
Photo courtesy of Visit Philadelphia

Afternoon
Three blocks south on Germantown Avenue, visit the Johnson House Historic Site, which was built in 1768 by an eminent Quaker family. They sheltered runaways escaping slavery on the Underground Railroad. Four blocks south is the Wyck Historic House and Garden, developed in the 1600s as a working farm; it has the oldest rose garden in the United States. On West Tulpehocken Street, find Ebenezer Maxwell Mansion, an imposing Gothic manor furnished with Victorian-era furniture and Egyptian-Revival stenciled walls. Ebenezer hosts Murder Mystery programs—this fall, it’s “Who Killed William Shakespeare?”

Evening
Dine at Mica, an epicurean restaurant named for the shimmering flecks in Wissahickon stone. Chef/owner Yianni Arhontoulis presents artistic dishes and a tasting menu inspired by seasonal ingredients.

Tip

On Second Saturdays, Historic Germantown opens all 16 historic sites from noon to 4 p.m. Buy the Historic Germantown Passport for discounted pricing for one visit to all 16 attractions: $25 for individuals and $45 for families.

brunch at cake
Photo courtesy of Visit Philadelphia

Day 3

Morning
Spend your final morning with a scrumptious brunch at Cake, a bistro enclosed in a sunny greenhouse. Then walk to Sunrise Lane, adjacent to Pastorius Park (a popular dog park), to see midcentury architecture by renowned American architects Robert Venturi and Louis Kahn. A pioneer in midcentury design, the Esherick House, demonstrates how Kahn turned a two-story concrete box into a fantastical structure. The Vanna Venturi House was built in 1964 by Robert Venturi, who’s recognized today as the father of postmodernism. These are not open to the public but a must for architecture fans.

woodmere art museum
Photo courtesy of Visit Philadelphia

Afternoon
Back in downtown Chestnut Hill, check out Artisans on the Avenue for locally made jewelry and funky fashion options. Style Camp, owned by a mother-daughter team, stocks lesser-known couture designers selling wearable statement clothing. Cartography buffs will appreciate The Philadelphia Print Shop with its vintage prints and historic maps. Open Thursday through Saturday, it’s time to graze at Market at the Fareway, a modern farmers market in an indoor/outdoor pavilion with 16 different vendors.

Evening
Finish your busy weekend at Iron Hill Brewery & Restaurant to sample a flight of craft beer and beer-inspired dishes like fish and chips infused with Vienna Red Lager and baby back ribs with Bedotter Ale barbeque sauce.

quiddich in philly
Photo courtesy of Visit Philadelphia

Save the Date

Chestnut Hill’s annual fall festival is Saturday, Oct. 19. Called Witches & Wizards (originally the Harry Potter Festival) the entertainment features free activities, Woodmere Art Museum Maze, the Love Cup Quidditch Tournament and a Brews & Broomsticks Pub Crawl.

This post originally appeared in our September 2019 issue as part of the Weekend Getaways cover story. For more travel content, subscribe to our newsletter.

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