Favorites for Winter/Holidays

Best Holiday Runs: North America

Here’s a reason to cheer a runner’s heart, despite the creeping cold and shorter days: holiday running! Travel magazines and websites are full of lists such as ‘best cities to see holiday lights”, so we did some research to match some of those with some great running routes. Our list of the best holiday runs in North America is a combination of beautiful light displays, festive shopping areas, and done-up neighborhoods. A special bonus: that dreaded nighttime run becomes a special treat! While the list might tilt toward wintry, northern spots, you’ll find some special surprises in warmer weather cities, too. For more, see our list of the best holiday runs in Europe.

New England-Y Holiday Runs. Here are some favorites if you’re looking for that Currier & Ives holiday run. Help here from the Boston Globe.

  • Boston. Our Back Bay tour is special during the holidays. Start at the Boston Common, site of a huge Christmas tree donated annually by Nova Scotia. Run along the Comm. Ave. mall amidst the brownstones, and then back along the festive Newbury St. shops.
  • Burlington, Vermont, where our highlights tour features the charming Church Street Marketplace and arts district
  • Portsmouth, NH, where you should focus on the center of town, Prescott Park, and the grounds of the Strawberry Bank Museum.
  • Portland, Maine, whose compact center is festive during the holidays, with charmingly lit indy shops, bars, and restaurants.
  • Kennebunkport, Maine, which has ropes of lights, wreaths, and greenery, the grand tree in Dock Square, and the lobster trap tree in Dock Square. Do a shore run by day and then a Christmas stroll by night!
  • Northampton, MA and the Five Colleges area in western Massachusetts.
  • Stockbridge, MA. The town that Norman Rockwell Captured for Christmas is charming. Be sure to run down Main St. and the historic Red Lion Inn. We even have a run around the grounds of the Norman Rockwell Museum!
  • Weathersfield, CT. A gorgeous run in this Hartford suburb, which has the largest historic district in Connecticut and does it up for the holidays. Hallmark filmed a Christmas movie there recently!
  • Newport, RI. Thousands of tiny white lights illuminate historic homes, shops, restaurants, and the bustling wharves, meant to represent candlelit homes during seafaring times. Newport has a month-long Christmas in Newport festival and several of the famous Mansions have decorated trees.

New York City. Here’s a good excuse vary from the usual Central Park or Hudson River running route. Manhattan is special at Christmas, with the famous tree and lights at Rockefeller Plaza, and the festive window displays on 5th Ave. and surrounding streets. Best bet for runners is to go early in the morning, while it’s still dark but to avoid the crowds.

Dallas. This city does it up for Christmas, but in a commercial sort of way. We have a route through the neighborhood of Highland Park, which is one of Dallas’ prettiest and most affluent neighborhoods, and a destination for light/decoration gawkers.

Kansas City: Plaza. The historic Plaza area is practically a tourist destination in itself during the holidays. Take a night run through this lovely area.

San Antonio Riverwalk. The River Walk and its adjacent streets are illuminated by tens of thousands of string lights, so it’s a treat to do a nighttime run there this time of year. You might have to dodge the crowds attending the nightly parade and the Fiesta de las Luminarias on weekends.

Newport Beach Boat Parade. Time your run to a nightly parade of more than 100 vessels adorned with lights and other decorations. Best viewed from our route on Balboa Island.

Detroit: Grosse Pointe Shores. This is a lovely neighborhood just northeast of Detroit. Run our route along Lakeshore Drive or in Jefferson to see gorgeous homes decorated done up for the holidays.

New Orleans: Garden District. We love the beautiful older homes that are gorgeously decorated during the holidays. From our Garden District run, make sure you hit First, Second and Pleasant Street.

Montreal: Old Montreal Tour. If you want a snowy run, Montreal is an almost sure bet. The beautiful older buildings, shops, and restaurants of Old Montreal have a particularly special glow at this time of year.