Those first flakes of snow have fallen, and for some, that brings stress rather than the anticipated joys of the upcoming holidays. The December festivities come with quite the to-do list—chores that can steal our moments of winter escape.
What if your holiday planning and shopping could come with an extra dollop of fun when done in getaway spots? Mark your calendars for these upcoming events and, rather than dread that to-do list, embrace, enjoy, and be entertained—all while finding great gifts and even some baking ideas.
### Winter Market at Encore Boston Harbor
Want to score some incredible gifts at great prices, all at a top Boston-area destination? There’s no gamble when heading to Encore Boston Harbor for their second annual Winter Market, taking place November 19–20 from 10 a.m. to 6 p.m.
You’ll find top brand cookware and housewares including Le Creuset, Yeti, Shark, fashion and accessories from brands like Coach, Brooks Brothers, and Patagonia, as well as electronics and gadgets from Apple and Boston Team Apparel. Most items are brand new; a few are gently used.
Here’s the mind-blower: prices range from just $1 to $40. That’s not a typo! This entire event benefits the Wynn Resorts Foundation’s Community Grant Fund, which supports non-profits and community initiatives across the Greater Boston area. Last year’s Winter Market Sale contributed nearly $340,000 to the fund.
The market takes place right in the resort, where you’ll find many great dining options, a beautiful casino, and top-notch holiday décor. Head in, shop for those dream gifts, and then enjoy even more fun afterwards. And with all you save on gifts, consider treating yourself to an overnight stay. They even offer a great bed and breakfast special.
### Holiday Cookie Research to the Max: Inn to Inn Cookie Tour
Imagine your friends inspiring your holiday baking plans while treating you to their freshly baked cookies—all served in a beautiful locale. It’s real, and it’s called the Inn to Inn Cookie Tour, a beloved holiday tradition in New Hampshire’s White Mountains.
This year’s tour takes place December 13 and 14. It’s a kind of holiday scavenger hunt, sending you to 11 unique and picturesque mountain spots in Tamworth, Madison, Eaton, North Conway, and Jackson. At each stop, you’ll sample cookies—both sweet and savory—chat with the bakers about the recipes, take home those recipes for your own use, enjoy holiday decorating, and more.
Expect special surprises like sleigh rides, live carolers, other live music, and a few on-site holiday markets where you can find unique gifts. Tickets sell out quickly, so be sure to act fast. A limited number of single-day tickets will be available online from December 2–8, 2025, for $35 per person.
To really amp up your experience and secure your spot, consider a VIP lodging package. It includes two nights’ accommodations, two cookie tour tickets, a 2025 holiday recipe book, a keepsake ornament, and a chance to win a $250 gift certificate. Some packages also include sleigh rides, dinners, or other seasonal extras. One-night packages are limited.
Find details and reserve your spot here: [Country Inns in the White Mountains](www.countryinnsinthewhitemountains.com/reserve-your-cookie-tour-package-now).
### More Than Just a Tour: Shopping, Dining, and Giving Back
While the tour itself can keep you busy both days, there are many ways to check off your holiday to-do list. In the valley of the already white-peaked Mount Washington, you’ll find great outlet stores and quaint shops. Spruce Hurricane, located in the center of North Conway, is a favorite, as is the old-school Zeb’s.
Countless amazing restaurants round out the experience, and of course, you can’t beat the most winter-perfect views around.
Like the Winter Market, your winter shopping escape here doesn’t just benefit your loved ones—it supports a great cause. Each year, participating inns donate a portion of tour proceeds to End 68 Hours of Hunger, a local nonprofit that fights food insecurity by providing meals to school children who might otherwise go without over the weekend.
Cookies, cooking ideas, decorations, and doing good—all while completing your holiday list. What could be better?
https://www.bostonherald.com/2025/11/16/who-says-holiday-prep-is-a-chore-check-out-these-shopping-escapes/
