Looking to get out of the city and visit Westport? Plan to skip the long lines and crowds of Black Friday shopping to #shoplocal and support the many small businesses that supported you during the last 18 months? There’s lots to do in Westport the weekend of November 26th-28th and lucky you, we’ve made it easy to hit all the stops and cross off all the items on your list.

Here are our suggestions for how to spend next weekend in Westport:

Friday November 26th: Let’s do a little Shop N Hop!

Starting early in the day, and staying open until 8pm, the shops of Westport participating in our annual Shop N Hop will have daily specials and smiling faces to greet you. Get your Shop N Hop Passport signed at all your stops along the way for your chance to win 1 in 3 GRAND PRIZES.

• 

• 

• 

• 

• 

• 

Suggested itinerary

Arrive early to do your shopping. Your first visit should be to Jake by the Lake-Life is Good where Cynthia and her team will have loot bags for the first 50 purchasing customers (min spend $100) plus $20 in gift cards per every $100 spent (can be used anytime after November 27th). Stop in at The Westport Brewing Company for lunch and a locally-made craft beer. Once you are fully satiated and thirst-quenched, make your way over to the WAC Westport Christmas Outdoor Market. Local artisans will be selling a wide variety of crafts, goods, and other treats. Take a short walk over to The Cottage Coffee House where they are doing a holiday pop-up with a special menu, “hot chocolate kits” and maybe pick up some freshly baked treats, like their ultimate cookie tray. Yum! Make sure to grab a horse & buggy ride around the village and don’t miss stopping by The Victorian Luxury Suites where Santa Claus will be hanging out from 4-8pm. If you are considering making Westport your home (you really should) then visit Watercolour Westport (off of Bedford St) for a home tour anytime between 9am and 7pm. Remember to drop off your completed Shop N Hop Passports to Jake by the Lake before 8pm to be entered into the Gran Prize draw. Your final stop should be to The Cove Inn for dinner and a show. On Friday November 26th, the Cove is presenting it’s Songwriter’s Circle with 4 very talented and amazing artists.

Make sure to stay the night because you aren’t going to want to miss what we have in store for you on Saturday November 27th. We suggest one of our many local Inns and BnB’s, like The Cove Inn, The Victorian Luxury Suites or The Black Dog Inn.

Saturday November 27th: Christmas continues in Westport!

Saturday will be jammed packed again with the Westport Market Christmas Edition, a Food Drive, the Rustic Winter Wonderland at Scheuermann Vineyard + Winery, and more music at The Cove Inn.

• 

• 

• 

Suggested itinerary

Sleep in. Grab some breakfast and something warm to drink from The Cottage Coffee House. Continue your shopping spree at many of the stores Westport has to offer. Pinecone, Rosie Yumski’s Fine Foods and Wags, Whiskers & Wings are a few of the many great options. Make your way over to The Westport Market Christmas Edition, taking place from 12-4pm. We hear they are maxed out on vendors spanning a wide variety of artisans and crafters. With this market being Christmas-themed, you are sure to find something for everyone on your list. Plus, #supportlocal. Also happening from 12-4pm, there will be a Food Blitz at Kudrinko’s in support of the Westport Food Bank. Stop by and be generous. Watercolour Westport is open again for home tours anytime between 9am and 5pm. Take a walk or a short drive and take a look at what living in Westport is all about. The Rustic Winter Wonderland is also happening on Saturday, from 1-5pm at Scheuermann Vineyard + Winery. Wander the property, drink in hand, visiting with more artisans and vendors, then grab a bite as Chef Francois will be cooking with fire! Sounds glorious! Finish off your day with music at The Cove Inn featuring sweethearts Head Over Heels and special guest Zack Colbert.

We’d love to have you spend the night once again as our innkeepers and lodging proprietors always have a warm and comfortable place to rest your head. See Friday night’s suggestions for who’d we recommend.

Sunday November 28th: Head home happy….or stay a while longer?

We know that after a full weekend of shopping and enjoying all that Westport has to offer, you’ll probably be looking forward to heading home. We hope that you’ll stay just a little while longer as there are still some great things to do in the village.

• 

• 

• 

Suggested itinerary

Zoom on over to Journey Fitness + Wellness for one of two sessions happening that day. We know Deborah would love to have you. Maybe continue with your self-care by heading up to Foley Mountain for a nature walk? It’s still quite beautiful up there and the views are always breathtaking. Definitely stop by Watercolour Westport for a home tour anytime between 9am and 5pm. Round out your day with a final visit to The Cove Inn for dinner and music by talented local musician Eric Uren.

So, we meant it when we said we’d like nothing better than to host you in Westport the weekend of November 26th-28th. There is just so much to see and do, you won’t want to miss it.