The holiday season is a wonderful time to visit Kittery, Maine. From local holiday markets and one-of-a-kind shops to waterfront dining and festive events, there's plenty to enjoy in this coastal town throughout November and December. Whether you're planning a weekend getaway or visiting for the day, here's how to make the most of the Christmas season in Kittery and the surrounding Seacoast.
Shop Local at Kittery's Holiday Markets
Holiday shopping is a little more fun when you can browse handmade gifts, meet local makers, and enjoy some seasonal treats along the way.
The Kittery Community Market is hosting two holiday events in 2026:
Outdoor Holiday Market | November 22, 10 AM–2 PM: Head to Post Office Square for a festive market featuring more than 35 vendors, local food, handmade gifts, winter greenery, and live music.
Holiday Sip & Shop | December 6, 10 AM–2 PM: Browse handmade gifts from 25 local artisans inside Blue Mermaid and Tributary Brewing Co. at 10 Shapleigh Road. Make a morning of it with brunch, local brews, and holiday shopping.
Both markets are great opportunities to support local businesses and find gifts you won't see in a typical department store.
Explore Kittery Community Market events
Find Unique Gifts in Kittery Foreside and the Outlets
Beyond the holiday markets, Kittery offers plenty of shopping opportunities throughout the season.
Start in Kittery Foreside, where independent boutiques, specialty shops, and local businesses make it easy to spend an afternoon browsing. Stop for coffee, explore the neighborhood, and pick up a few gifts along the way.
For a bigger shopping trip, head to the Kittery Outlets along Route 1. With a wide selection of stores, it's a convenient place to tackle your holiday shopping list.
Don't forget the Kittery Trading Post, a longtime local favorite for outdoor gear, clothing, Maine-made gifts, and more.
Enjoy Holiday Dining in Kittery
After a day of shopping, settle in for a good meal at one of Kittery's local restaurants.
Kittery Foreside has a great selection of restaurants, from casual neighborhood spots to places worth planning an evening around. Whether you're meeting friends for lunch or enjoying a relaxed dinner, there's no need to travel far.
For something hearty after a chilly day, stop by Ore Nell's Barbecue for Texas-style barbecue, smoked meats, and comforting sides.
You can also explore our Kittery Dining Guide for more local recommendations.
Experience More Holiday Traditions Across the River
One of the best things about staying in Kittery is having downtown Portsmouth, New Hampshire, just across the Piscataqua River. During the holiday season, it's worth setting aside an afternoon or evening to enjoy some of Portsmouth's favorite traditions.
Candlelight Stroll at Strawbery Banke Museum | December 4–6, 11–13 & 18–20, 2026
Step back in time as Strawbery Banke's historic homes are decorated for the holidays. Wander through the candlelit museum grounds, learn about seasonal traditions from costumed interpreters, and enjoy live music and festive displays.
Learn more about Candlelight Stroll
Portsmouth Illuminated Holiday Parade & Tree Lighting | December 5, 2026
Downtown Portsmouth comes alive for its annual holiday celebration. The festivities begin with the Market Square tree lighting at 5 PM, followed by the illuminated parade at 6 PM. It's a favorite local tradition and a fun way to kick off December.
While you're in Portsmouth, browse the downtown shops, enjoy the seasonal decorations, or make dinner reservations before heading back to Kittery.
Make a Holiday Weekend of It at The Water Street Inn
With holiday shopping, seasonal events, and great dining on both sides of the river, there's plenty to fill a December weekend in Kittery.
The Water Street Inn offers a comfortable home base for exploring the area. Located along the Piscataqua River in Kittery, our boutique inn puts you close to Kittery Foreside, local restaurants, shopping, and downtown Portsmouth.
Spend your days exploring the Seacoast, then return to a quiet waterfront setting at the end of the evening.
Planning a holiday getaway to southern Maine? Explore our rooms and make The Water Street Inn part of your Christmas season.