Couples

Winchester Amore

AFTERNOON

Arrive in Winchester and check into your accommodations. From modern hotels to charming inns, many are just minutes fromOld Town Winchesterand the heart of the Festival. Settle in and get ready for an unforgettable weekend!

EVENING

Head to Old Town Winchester for a delicious dinner. With a variety of restaurants offering everything from upscale dining to casual bites, there’s something for every taste.

MORNING

Start your day with a n American-style breakfast at Uno’s Pizzeria at The George Washington Hotel  in Old Town Winchester. Known for its variety of breakfast favorites, it's the ideal fuel for a day full of festivities.  Walk through Downtown Winchester and visit George Washington’s Office Museum.

MIDDAY

Spend the afternoon at the beloved Bloomin’ Wine Fest starting at 11:00 a.m. Sample wines from over 20 Virginia wineries and enjoy selections from regional craft breweries. The festival atmosphere is complete with live music, local artisan booths, and mouthwatering festival food - all in the heart of historic Old Town.

EVENING

Wrap up your Saturday with unforgettable live entertainment at The Bright Box in downtown Winchester. From dynamic performances to great drinks and vibrant energy, it’s the perfect spot to spend your night out. Enjoy top-tier acts, lively crowds, and a one-of-a-kind atmosphere that keeps the good times going. A local favorite you won’t want to miss!

MORNING TO AFTERNOON

Visit the Museum of the Shenandoah Valley, open from 10 a.m. to 5 p.m. Tour its inspiring exhibits, walk through 7 acres of blooming formal gardens, and relax in the city’s largest green space—an oasis of springtime color.



Before heading home, enjoy one last local tradition: a leisurely country drive to a nearby apple orchard in full bloom. The stunning pink and white blossoms, set against the backdrop of the Blue Ridge and Allegheny Mountains, are a picture-perfect ending to your Shenandoah Apple Blossom Festival® getaway.