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. A good strategy for finding a pretty holiday run in any city is to search our ‘Fantastic Neighborhoods‘ category. 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.
  • Manchester, VT. Do a run through the beautiful viillage.
  • 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!
  • Mystic, CT. Do our Mystic Seaport Loop at night to see illuminated boats and a lantern light tour
  • 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/New Jersey Area. 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. For some pretty neighborhoods, head to Park Slope in Brooklyn, our Port Washington route on Long Island, the historic Montrose District in South Orange, NJ, and Princeton’s residential neighborhoods.

Saratoga Springs. Festive shops give way to gorgeous older homes along Broadway Ave.

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.

Ann Arbor. A particularly festive town during the holidays, known for its outdoor markets.

Duluth. The Lakewalk route features Bentleyville, a massive light display.

Chicago. The Magnificent Mile on Michigan Ave. has great lights and holiday window displays.  North Shore neighborhoods of Highland Park, Glencoe, Winnetka have gorgeous homes all done up for the holidays.

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.

Branson, MO. Home of the Ozark Mountain Christmas.

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.

Beaufort, SC. Known for its Crystal Coast Christmas Flotilla.

Greenville, SC. Makes lots of lists for its particularly festive downtown scene during 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.

St. Augustine, FL. Lights, candles, and Christmas decor are sprinkled throughout the town’s historic district.

Jackson, WY. In downtown, the famed arches of elk are wrapped with lights.

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.

Carmel-by-the-Sea. There might not be snow, but there are Christmas lights, wine tastings, and beach sunsets.

Canada: Three routes to seek out that combine holiday lights with a truly winter atmosphere and a holiday glow are our Old Montreal Tour, historic Quebec City Tour, and the scene in downtown Banff.