Winter Date Night Ideas Across the Main Line Region

Why venture into Philadelphia when the western suburbs have such an abundance of romantic date activities for you and your partner?

With holiday magic alive and Valentine’s Day on the horizon, it seems like the most romantic time of the year. Fortunately for us, the Main Line region offers a flawless backdrop for romantic excursions, whether you’re planning a first date or a night out with your long-term significant other. Here are ideas for what to do on your next local date night.

Longwood Gardens

1001 Longwood Rd., Kennett Square, (610) 388-1000


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Over 200 acres of gardens come alive with spectacular holiday lights and wintery blooms. It’s the perfect location for taking a romantic walk hand-in-hand while exploring the festive displays and conservatory. For an extra dash of romance, check out the Indoor Performing Series to share in an enchanting blend of movement and sound. 

Lancaster County Farmers Market

389 W Lancaster Ave., Wayne, (610) 688-9856

Visit this indoor food market for a more casual meet-up. Whether your date fancies sampling local produce from Herrcastle Farm, home-baked biscotti at the Ultimate Bake Shoppe or a hand-rolled “Philly Dilly” pretzel from Country Twist, all your bases will be covered. Stroll around the stalls and enjoy each other’s company amidst the foodie sounds and smells.

Local Wineries 

Various locations


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If you’re a wine aficionado, you can impress your date with a visit to one of the many beautiful wineries in Chester County. While sipping wines from around the world and considering their tasting notes, you’ll have a chance to appreciate your partner’s unique qualities, too, and allow your romantic bond to flourish.

Bryn Mawr Film Institute

824 Lancaster Ave., Bryn Mawr, (610) 527-9898

This classic date night will never get old! Enjoy a movie night at the historic 1920s Bryn Mawr Film Institute, a stylish venue with character that’s perfect for catching the latest movies or vintage re-runs. Plenty of restaurants and bars are nearby if you fancy grabbing a bite to eat afterwards.

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Enjoy Live Music

Various locations


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Kennett Brewing Company is a fun venue with live music from local bands, open-mic nights and a wide range of brews. It even throws a trivia night if you want to amaze your date with your general knowledge. Likewise, 118 North is popular for live music with an eclectic mix of shows, happy hour from Wednesday to Sunday and delicious food options.

Ground Provisions

1388 Old Wilmington Pke., West Chester, (610) 355-4411

If you’re looking for something swankier, consider this charming eatery where every plate is a work of art. The food is entirely plant-based, pulling from local farms. Try the five-course tasting menu with a wine pairing option in an intimate nine-table dining room or take a seat on the front porch for tapas and a glass of natural wine, local beer or specialty cocktail.

Related: Where to Go Skiing Near the Main Line This Winter

Our Best of the Main Line & Western Suburbs Party is July 25!