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holiday specials

2022 Holiday Events, Shopping, and Dining in Middletown, CT.

Celebrate the fun-filled holiday season with Inn at Middletown. Discover the wonders of festive spirits and snap pictures to create memories with your family and friends. Enjoy the Magic of Middletown with dazzling tree lighting, shop for your loved ones at Tesoro Unique Treasures and Gifts, and munch on some seasonal treats at great restaurants like Tavern at the Armory and La Boca. Start planning your holidays with our latest specials and events.
Local Events

36th Annual Holiday on Main Street "Magic of Middletown"

Main Street, Middletown CT
Date & Time: Various Dates and Events

Holiday Bazar

Wadsworth Mansion, Middletown CT
December 4th from 10 am- 3 pm

Annual Handel Messiah Sing or Listen

The Kate (Katherine Hepburn Theater) Old Saybrook, CT
December 18th at 2 pm
Holiday Shopping

Perratti's Country Barn and Christmas Shop

288 Baileyville Road, Middletown, CT

A Pocket Full of Posies

386 Main Street. Middletown, CT

Tesoro Unique Treasures and Gifts

484 Main Street, Middletown, CT
Holiday Dining

Tavern at the Armory

Sun-Sat from 4:30 pm- 9 pm
70 Main Steet, Middletown, CT
Comfy eatery with upscale American dishes

Esca Restaurant and Wine Bar

Sun-Sat from 11 am-12 am
437 Main Street, Middletown, CT
Upscale Italian dining destination

La Boca

Sun-Sat from 4:00 pm - 1 am
337 Main Street
Lively Mexican Restaurant with a big drink menu and live music


“Santa’s Suite Life” Shop and Stay local

“Santa’s Suite Life” Shop and Stay local

  • Relax in our 2-room suite with a complimentary bottle of wine and cheese tray
  • Receive a $50 voucher at check-in to use at Tavern at the Armory
  • Rate: $299