ShopDowntownSince 1999
Crowds on the Loudoun Street Mall after the Christmas parade, Winchester, Va.
Home › Stories

Stories · Holiday 2026

Christmas on Main Street

Three guides to the small towns that do the holidays best, with every date checked against the people who run them, plus a gift guide to shop originals from seven small town stores and ten downtown breweries made for a shopping break.

Browse by section · Shop, Dine, Play, Stay →

Crowds on the Loudoun Street Mall after the Christmas parade, Winchester, Va.

New · Dec. 1–24

24 Days of Downtown: Will Your Town Be Featured?

A new door opens every day through Christmas Eve: a downtown shop, inn, show or table, picked by the editors. Tune in daily, and nominate your favorite.

  • Shop, Stay, Play, Dine
  • 24 towns, no town twice
  • Hanukkah nights, Dec. 4–11
  • Nominations open now
The twin spires of the Cathedral of St. Helena, Helena, Mont.

Play · A Sunday read

7 Historic Downtown Churches With Magnificent Steeples

A shingled chapel beneath Castle Rock, a golden hand over Mississippi, and the lanterns of 1775: seven spires that still define their Main Streets.

  • Green River, WY
  • Savannah, GA
  • Port Gibson, MS
  • Litchfield, CT
  • Providence, RI
  • Boston, MA
  • Helena, MT
The neon Route 66 shield in Route 66 Park, Joliet, Ill.

Route 66 Downtowns · Part 1 of 7

Route 66 at 100: An Illinois Road Trip Through Six Main Street Downtowns

The Mother Road turned 100 on Nov. 11. Start the drive west with six Illinois downtowns, two roadside giants and lunch at a café founded in 1924.

  • Joliet, IL
  • Wilmington, IL
  • Pontiac, IL
  • Atlanta, IL
  • Springfield, IL
  • Litchfield, IL
A Christmas tree farm in Ashe County, N.C.

Holiday 2026 · Family day trips

Christmas Tree Farm Road Trips: Cut Your Own, Then Lunch Downtown

Six choose-and-cut farms, each paired with a small-town Main Street close by for lunch, a parade or a visit with Santa.

  • West Jefferson, NC
  • Littleton, NH
  • Media, PA
  • Wooster, OH
  • Snohomish, WA
  • Montrose, CO
Victorian storefronts on Main Street in Ferndale, Calif.

Day trips · Art on Main Street

6 Small Town Art Galleries Worth the Drive

A depot with a caboose out front, a co-op that bought its building with painted pigs, and a schoolhouse full of Georgia pottery.

  • Watkinsville, GA
  • Brandon, VT
  • Lanesboro, MN
  • Red Lodge, MT
  • Jerome, AZ
  • Ferndale, CA
Main Street at night, Annapolis, Md.

Holiday 2026 · Events calendar

Holiday Open Houses and Late Shopping Nights Downtown

Ten downtown evenings and afternoons when the shops stay open, pour cider and decorate the windows, with dates checked against each organizer.

  • Madison, GA
  • Norcross, GA
  • Bainbridge, GA
  • Thomasville, GA
  • Thomasville, GA
  • Madison, IN
  • Annapolis, MD
  • Ann Arbor, MI
  • Sterling, IL
  • Cuero, TX
Main Street, Franklin, N.C., with the Nantahala mountains beyond

Holiday 2026 · Gifts for athletes

7 Downtown Sports Shops for the Athlete on Your List

Running shoes fitted by hand, team jackets, bikes and ski gear from sporting goods stores that still sit on Main Street.

  • Newnan, GA
  • Senoia, GA
  • Covington, KY
  • Huntington, WV
  • Wausau, WI
  • Flagstaff, AZ
  • Franklin, NC
Carved trout on the front of Dan Bailey's fly shop, Livingston, Mont.

Holiday 2026 · Gifts for anglers

9 Downtown Fly Shops to Catch a Gift for Your Angler

Gift cards, shop-logo hats and guided days from fly shops on Main Street, each a short walk or drive from its home river.

  • Sylva, NC
  • Blue Ridge, GA
  • Clarkesville, GA
  • Roscoe, NY
  • Durango, CO
  • Livingston, MT
  • Ennis, MT
  • Missoula, MT
  • Ketchum, ID
Storefronts in downtown Clayton, Ga., below the Blue Ridge Mountains

Holiday 2026 · Coffee before the shops

10 Downtown Cafés for a Christmas Latte Before You Shop

A white mocha in the Blue Ridge, eggnog by the Columbia River Gorge and house-made gingerbread syrup in central Vermont.

  • Clayton, GA
  • Canton, GA
  • Columbia, TN
  • Charlottesville, VA
  • Lititz, PA
  • Barre, VT
  • Galena, IL
  • Fredericksburg, TX
  • Jackson, WY
  • Hood River, OR
Patio tables outside the Brick Store Pub on Decatur Square, Decatur, Ga.

Downtown breaks · Taprooms near the shops

10 Downtown Breweries Made for a Shopping Break

A Georgia lager in a 1940s tire warehouse, a pint in an old Greyhound station and a brewpub inside Frederick’s first city hall.

  • Athens, GA
  • Decatur, GA
  • LaGrange, GA
  • Ogden, UT
  • Paducah, KY
  • Frederick, MD
  • Sheridan, WY
  • Dubuque, IA
  • Staunton, VA
  • Macon, GA
The street clock on Broad Street, Thomasville, Ga.

Holiday gift guide · Shop originals

7 One-of-a-Kind Gifts From Small Town Shops This Christmas

A truffle filled with North Georgia port, a leather crossbody from a Savannah studio, and a soap bar named for a hometown movie.

  • Thomasville, GA
  • Savannah, GA
  • Dahlonega, GA
  • Roswell, GA
  • Natchitoches, LA
  • Annapolis, MD
  • Rockland, ME
Christmas lights along the Cane River, Natchitoches, La.

Holiday guide · Decorated downtowns

The Best Christmas Towns to Visit in 2026: Five Decorated Downtowns for Holiday Shopping

Courthouse domes outlined in white, carolers in top hats, and shop windows worth crossing the street for.

  • Natchitoches, LA
  • St. Charles, MO
  • Ogden, UT
  • Annapolis, MD
  • Marshall, TX
Crowds on the Loudoun Street Mall after the Christmas parade, Winchester, Va.

Holiday guide · Christmas markets

Small Town Christmas Markets 2026: Five Main Streets Worth the Trip

Wooden huts on the square, mulled cider in mittened hands, and makers who live a few blocks away.

  • Easton, PA
  • Carmel, IN
  • Medina, OH
  • Franklin, TN
  • Winchester, VA
The lobster-trap Christmas tree in Rockland, Maine

Holiday guide · Tree lightings

Christmas Tree Lighting 2026: Five Main Street Ceremonies You Don't Want to Miss

A countdown on the courthouse lawn, a brass band, and a whole town gasping at once when the switch flips.

  • Grapevine, TX
  • Coeur d'Alene, ID
  • Rockland, ME
  • Holly, MI
  • Mount Airy, NC

About these guides

ShopDowntown covers the 1,194 towns with Main Street programs across America. Our holiday stories favor walkable, historic downtowns over malls and theme parks, and we link every pick to its organizer’s official site and, where we have one, to the town’s ShopDowntown guide.

Know a downtown that belongs on next year’s list? Tell us through the form.

The Daily Downtown Digest

Get picks like these in your inbox

New downtown finds, events and deals, two or three times a week, with day trips close to home.

  • New downtowns on the map
  • Merchants worth the drive
  • Events this weekend
  • Main Street deals
  • A story of the day
  • Day trips near you

Unsubscribe anytime, and we never sell your address. Privacy

For downtowns & shop owners

Put your downtown or shop in the Digest

Main Street programs, downtown authorities, chambers, shops, inns and makers: tell us what’s happening and our editors will consider it for an upcoming issue.

Tell us about your downtown or shop

Downtown teams and owners get the Digest every morning. We read every note and our editors choose each issue; featured placement for shops is a simple monthly plan.

Photos from Wikimedia Commons: Crowds on the Loudoun Street Mall after the Christmas parade, Winchester, Va.: Fuzzykittenhead, CC BY 3.0; The twin spires of the Cathedral of St. Helena, Helena, Mont.: Royalbroil, CC BY-SA 4.0; The neon Route 66 shield in Route 66 Park, Joliet, Ill.: Dough4872, CC BY-SA 4.0; A Christmas tree farm in Ashe County, N.C.: Indy beetle, CC0; Victorian storefronts on Main Street in Ferndale, Calif.: Ellin Beltz, CC BY-SA 3.0; Main Street at night, Annapolis, Md.: Andrew Parlette, CC BY 2.0; Main Street, Franklin, N.C., with the Nantahala mountains beyond: w_lemay, CC BY-SA 2.0; Carved trout on the front of Dan Bailey's fly shop, Livingston, Mont.: Mike Cline, Public domain; Storefronts in downtown Clayton, Ga., below the Blue Ridge Mountains: Harrison Keely, CC BY 4.0; Patio tables outside the Brick Store Pub on Decatur Square, Decatur, Ga.: Marc Merlin, CC BY-SA 4.0; The street clock on Broad Street, Thomasville, Ga.: Michael Rivera, CC BY-SA 3.0; Christmas lights along the Cane River, Natchitoches, La.: Wikilester 3, CC BY-SA 4.0; The lobster-trap Christmas tree in Rockland, Maine: Susan Bell, CC BY 2.0.

ShopDowntown appNew stories on your phone as they landGet