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Local shopping, Savvy+Grace (Photo: Caroline C. Barney)

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30 Day Gratitude Challenge

Re-Centering Ourselves for the Holiday Season

grat·i·tude: The quality of being thankful; readiness to show appreciation for and return kindness.

It's that time of year again, the time when we rush toward the holidays in a frenzied state of acquiring joy. Families come together. Generational food rituals are elevated. Gifts are acquired at a dizzying pace. Social gatherings are taken to another level. The lists are long, and the line between celebration and exhaustion is as precarious as walking on a tightrope.

Every year, I tell myself that this year will be different. This year, I'll approach the holiday season in a more measured way—holiday chill, balanced. I've got this all figured out. And then mid-November arrives, I find myself in the Starbucks drive-through, determined to get my hands on a hot mocha-something-or-other in the newly released holiday cup just so I can "feel festive" while embarking on the seasonal hustle and bustle. It dawns on me—I'm doing it again.

This year, let's consider a new idea: a gratitude challenge. Perhaps it will help us shift our perspective, or at least the intention to do so, and re-orient our actions, allowing us to view the holiday buildup in Westport through a different lens.

The Westport 30 Days of Community Gratitude

Day 1: Kick off the month by taking a CLOOP (Compo Loop). Begin at the playground, walk past the baseball fields up to the slipway, continue down South Beach to the cannons, and return to the playground.

Day 2: Step outside and name three things that amaze you. The white oak is our state tree and is truly magnificent. Do you have one nearby?

Day 3: Take a walk! The Library Riverwalk & Garden is a spectacular option that leads you behind the Levitt to an incredible view of the Saugatuck River.

Day 4: Allow yourself to enjoy the extra hour of sleep tonight. But don't forget to change your clocks.

Day 5: Take a moment to watch the birds in action throughout town. Thanks to ongoing conservation efforts, we continue to be surrounded by stunning feathered friends. If you have extra time, consider visiting the Winged Wonders bird demonstration at Earthplace at 1 p.m. today.

Day 6: Turn on your faucet and reflect on the gift of clean, running water.

Day 7: Skip social media and try something new. We have no shortage of creative options in town. In fact, today, The Westport Museum offers free admission to explore everything they have to offer.

Day 8: Write a thank-you card and mail it to our Westport Fire Department (515 Post Road East) or our Westport Police Department (50 Jesup Road).

Day 9: Reflect on all the fresh food available to us in town. Today is the last day of the season for the Westport Farmers Market at 50 Imperial Avenue. Take a stroll through the stands, experience farm-fresh food, and meet some local growers.

Day 10: Donate something (time, clothes, money, books, etc.). The Goodwill drive-through, 1700 Post Road East, is open for donation drop-offs from 9 a.m. to 7 p.m. Mon-Sat and from 10 a.m. to 7 p.m. Sundays.

Day 11: Thank a veteran in town or consider cheering for or taking part in the 2nd annual Honor Our Veterans 5k at Sherwood Island at 9 a.m.

Day 12: Watch the sunrise at Old Mill Beach or Compo at approximately 6:30 a.m. Don't worry; no one will judge you if you're still in your pajamas. We might be in ours too.

Day 13: Recognize three things you sometimes take for granted.

Day 14: Read something positive and inspiring. Our town is filled to the brim with talented, thoughtful writers; you won't have to look far. In fact, the Westport Writers Workshop is hosting a Mindful Writing event today from 10 a.m. to 5 p.m. Maybe you'll be the one writing the inspiring words.

Day 15: Open the door, step outside, and take a deep breath. That's it. Even this simple act can be profound.

Day 16: Try to go through the whole day without complaining. Try smiling and waving at the teams working on the Post Road construction instead of feeling frustrated with the inconvenience.

Day 17: Call a friend you haven't spoken to in a while. Not a text. A call. Like it's 1990, and you have to drag the phone and its extension cord into another room to not be heard by the rest of your family.

Day 18: Take a photo of something you're grateful for in Westport. We'd love to see what you choose—post your photo and tag us! @westportlifestyle.

Day 19: Actively LISTEN to everyone today.

Day 20: Write down three people in Westport who inspire you, and if you're up for it, reach out and let them know. This list could go on for days for me, but if you're looking for a few ideas, visit the town's Community Organizations page, and you will be in awe of the number of impactful organizations we have in town. (On - Google it.)

Day 21: Take a drive down Main Street and as you pass Town Hall, think of all the people working hard to make our town great.

Day 22: Go outside tonight and look at the stars. If you'd like to take your stargazing to another level, there is a Star Party at the Westport Observatory at 8 p.m. tonight.

Day 23: Stop, listen, and look today. Try not to let the day pass by without pausing to reflect on who and what you are thankful for. Happy Thanksgiving, Westport—we're thankful for all of you!

Day 24: Shop local and let them know you appreciate all that goes into following a dream and building a business. WEST, Savvy+Grace, Kawa Ni, Don Memo, Millie Rae's, and so many others.

Day 25: Do one random act of kindness for someone in town. Smile at them, buy their coffee, tell them they look great.

Day 26: Sit still for 10 minutes and listen to the sounds around you.

Day 27: Offer to do something unexpected for a loved one. You can never go wrong with a bouquet of flowers or a plant from Trader Joe's.

Day 28: Watch the sunset from the back parking lot of Longshore. It might be the best place in all of Westport for it. Drive through the golf course and through the course parking lot on your right to the lower lot, scout through the trees and grasses to a small stretch of beach. It sets at 5:45 p.m. - See you there!

Day 29: Did you learn anything new about yourself or our community this month?

Day 30: How will you continue your gratitude practice? Here are some ideas: Make a meal for the Gillespie Center, Donate toys to the PAL Toy Drive, support the arts by going to the Westport Country Playhouse or MoCA Westport, donate your no-longer-used holiday decorations, clothes, and household items to Goodwill, 1700 Post Road East, open from 7 a.m. to 9 p.m. every weekday and 10 a.m. to 7 p.m. on Sundays. Just drive through and drop it off.

Oh - and never underestimate the power of a smile.

Caroline is a bestselling author, inspirational speaker, consultant and coach. Her work focuses on helping others build lives and organizations that are purpose-driven, joy-filled and resilient.

  • Library and Garden Walk. (Photo: Caroline C. Barney)
  • Westport Police Department (Photo: Caroline C. Barney)
  • Local shopping, Savvy+Grace (Photo: Caroline C. Barney)
  • Westport Town Hall (Photo: Caroline C. Barney)
  • Westport Museum for History and Culture (Photo: Caroline C. Barney)
  • Bird spotting.
  • Farmers' Market.
  • Thank the Westport Fire Department.
  • A November view of Wesport Library and Levitt Pavilion. (Photo: Jerri Graham)
  • Caroline C. Barney (Photo: Jerri Graham)