Make It a Date Night (or Day!)

Two is the magic number. You and your sweetie can connect without the kids, celebrate an anniversary or explore new places as empty nesters. Even create a fresh tradition with new love. Set the cellphones to vibrate and find new vibrations as you dine and play your way across Chicago’s North Shore — night or day! 
 

Pescadero, Wilmette

Table for Two
Linger over a delicious meal free of distractions (or chores) in some tasty places. The Capital Grille (Old Orchard Rd. & Skokie Blvd., Skokie) in Westfield Old Orchard will spoil you for any milestone. “Comfortable elegance” surrounds as you indulge in dry-aged steaks, fresh seafood and world-class wines. Fresh and fabulous, Pescadero Seafood & Oyster Bar (1167 Wilmette Ave., Wilmette) has a mod vibe with neighborhood charm. The upscale, maritime-themed seafood establishment rolls out a killer Raw Bar or go full-on Surf & Turf.
 

Guildhall Restaurant, Glencoe

Wining and Dining
Guildhall Restaurant (694 Vernon Ave., Glencoe) shows off their American bistro with Euro-flair offering temptations from Alaskan Maki (snow crab, fresh salmon, mango, asparagus, serrano, salmon roe, yuzu) to Berkshire Pork Chop (with celery and fennel coleslaw, roasted grapes and jus). For a more casual evening (think less wine, more brews), head over to District Brew Yards (700 N Milwaukee Ave., Wheeling) for this brewery meets beer hall space for an evening of cold drafts, tasty BBQ, tacos, sandwhiches and more. 

Pinstripes, Northbrook

Get a Move On 
Play bocce or lace up your bowling shoes for the classic pastimes at Italian/American bistro Pinstripes (1150 Willow Rd., Northbrook). Hike the River Trail Nature Center (3120 Milwaukee Ave, Northbrook) with walking trails to work out together or just meander. The center’s educational displays or self-guided tours are at your own pace or pick an event to meet a beekeeper or play a scavenger hunt. Fuel up first at Glenview Grind (1837 Glenview Rd., Glenview) with faves like the Matcha Green Tea Latte or Iced Frango Mint Latte and breakfast sandwiches. Dust off your bikes (or bicycle-built-for-two) on the Green Bay Trail (400 Maple St., Winnetka) for a late afternoon ride and finish up at Hometown Coffee & Juice (749 Elm St., Winnetka & 700 Vernon Ave., Glencoe) for smoothies and bagel melts. The asphalt path runs two-plus miles through the Village of Winnetka, from Kenilworth to Glencoe, paralleling the Metra commuter line. 
 

Evanston SPACE

That’s Entertainment!
Sit back and enjoy the show with oodles of choices from the area’s enviable range of world-class theaters and music venues. From big stages like Ravinia (200 Ravinia Park Rd., Highland Park) to more intimate venues like Evanston SPACE (1245 Chicago Ave., Evanston) and cozy theatrical experiences, you’ll find every genre and frequent world premieres. Focus your choices on this incredible feast of live performances along with our complete lineup of upcoming events on Chicago’s North Shore Event Calendar for any night of the week, all year round. It’s got all kinds of art exhibits and special fests, too. When you end up on Chicago’s North Shore, your extensive dining options will round out a beautiful time.