Breathtaking mountain views, antique farmhouses, and winding roads are hallmarks of this cluster of resort towns. But tying the knot here offers its own charms, such as treating guests to local bluegrass music, s’mores roasts, or dessert receptions at Tanglewood. At the Cranwell Resort, set on a hilltop, old-world elegance abounds: Its 19th-century mansion boasts sweeping panoramas of the area’s rocky terrain and lush foliage. Ceremonies on the property’s manicured lawn get a dose of drama from a grand staircase entrance on the outdoor terrace; an intimate ballroom brings nature indoors with 10 floor-to-ceiling windows; and the 35,000-square-foot spa is the ultimate spot for a prewedding facial or massage. Alternatively, hold your reception at Gedney Farm in New Marlborough, where couples exchange vows on a grassy knoll and party in a three-tiered barn. Locally sourced favors range from the quaint (Berkshire Berries’ jams and maple syrups) to the urbane (cognac-infused bonbons and other handcrafted sweets from Lenox-based Chocolate Springs). It’s enough to make you forget you’re only about two hours from home—that, and a few glorious centuries back in time. –Brittany Jasnoff
Venues: The Cranwell Resort, 55 Lee Rd., Lenox, 800-272-6935, cranwell.com; Gedney Farm, 34 Hartsville–New Marlborough Rd., New Marlborough, 413-229-3131, gedneyfarm.com.
Rehearsal Dinner: Bistro Zinc, 56 Church St., Lenox, 413-637-8800, bistrozinc.com.
Wedding Planner: Clover Bell-Devaney, Impeccable Events, 21 St. James Ave., Lee, 413-441-1657, impeccableevents.org.
Photographers: Tim Ryan Smith, 479-790-7249, timryansmith.com; Gina Renzi Photography, 518-226-4498, ginarenziphotography.com.