James Bartlett Littlefield

James Bartlett Littlefield (Bart to all) died peacefully in his sleep at home in Concord, Massachusetts, surrounded by his loving family. He was 67. He was diagnosed with advanced prostate cancer just a year before his death. 

Bart was born on October 7, 1958, with an irrepressible twinkle in his eyes, the only child of Jack and Bobby Littlefield, who raised him in Riverside, CT. Bart’s family was very active and, naturally, so was Bart. He came from a long line of accomplished sailors and quickly distinguished himself on the water. His family and innumerable friends spent summers on Bakers Island off the coast of Marblehead, MA where the intrepid Littlefields enjoyed their cherished oceanside cottage with no electricity and minimal amenities. It was their happy place treasured by many for old fashioned good times. In his youth, Bart was legendary on Long Island Sound for his racing prowess. He also loved performing, especially in musicals, where his tenor voice delighted audiences and friends alike. When he was not on the water or on the stage, Bart could often be found flying down a ski slope, seeking out whatever mountain or hill he could find. 

Bart attended Greenwich High School, Dartmouth College, and the Stanford Graduate School of Business. He excelled academically while engaging fully in the communities around him. His huge heart, boundless enthusiasm, and natural curiosity drew people to him everywhere he went. Bart approached life with joy and optimism. “No” was rarely in his vocabulary. With his infectious smile, kind spirit, and eagerness to embrace every opportunity, he formed lifelong friendships wherever life took him. 

Bart met Bar Gooding on a blind date arranged by his first cousin, Heidi Harring. From that moment on, they were inseparable. He is survived by his beloved wife, Bar; his sons, Rex, Jack, and George; his daughter, Margot; his daughter-in-law, Caroline; first cousins John Reichenbach, Heidi Harring, Fritz Reichenbach, Bill Kingsbury, and Jim Kingsbury; as well as numerous brothers- and sisters-in-law, nieces, nephews, godchildren, and countless dear friends. 

Bart was fast at many things sailing, skiing, biking, running, solving the NYT crossword puzzle, and identifying airplanes. He earned his pilot’s license and pursued his passion for aviation by joining Northwest Airlines/Republic Airlines, now Delta. He could identify virtually any aircraft, stationary or in flight, and always did. After eight years in Minneapolis, Bart moved to Boston to run Northwest’s operations at Logan Airport. 

Always fascinated by emerging technology and changing consumer behavior, Bart recognized opportunities in the rapidly developing internet economy. He built and sold several successful digital travel companies and continued pursuing his passion for travel and innovation through his most recent venture in the private jet charter business. 

While Bart loved and pursued many interests, his family meant everything to him. He wanted to show his children the world as he experienced it, on skis, on sailboats, in hiking boots, on bicycles, in museums, and in theaters, and he did exactly that. He and Bar created a life rich in adventure, learning, laughter, and love. 

Bart gave generously of his time and talents to the communities he cared about. He co-ran the Buddy Werner Ski Program at Nashoba Valley. He served as Commodore of his beloved Sakonnet Yacht Club and continued to contribute as a member of its Board of Governors. At Trinitarian Congregational Church, he served as a Deacon and on numerous committees, with the Mission Committee holding a special place in his heart. 

Bart was a devoted graduate of Dartmouth College. He embraced everything it had to offer. His Psi Upsilon fraternity brothers became true lifelong brothers, and his Class of 1980 became an enduring source of friendship, purpose, and joy. He gave tirelessly to the Dartmouth community and received immeasurable fulfillment in return. 

Bart was also committed to civic affairs and served the Town of Concord as a dedicated member of the Election Committee. No matter the cause, Bart was always among the first to volunteer. Helping others came naturally to him. 

Music was another lifelong passion. After college, he joined the Bosstones, an a cappella group of former college singers that regularly and theatrically performed at Faneuil Hall to the delight of tourists and locals alike. Bart rarely missed a Steely Dan concert in New England. When friends were “unavailable”, he happily attended alone and inevitably left with new friends. 

The Concord Runners were a daily part of Bart’s life for decades. As many runners gradually became cyclists, Bart embraced both pursuits, running and biking in all weather. Whether riding in Concord, Vermont, France, Italy, or Spain, he was always in search of the steepest hill and thrilled in the camaraderie of his fellow extreme riders. 

His love of cycling extended to Little Compton, RI, a very special place in his heart. There, Bart was a familiar presence on the daily Sakonnet rides and could often be found lingering over conversation at the Art Café well after the ride was over. In Little Compton, he was also a fierce competitor in the Alden fleet, sailing his beloved Bachelor Button every Saturday afternoon with his crew and racing partner. While the competition on the water was intense, the storytelling and laughter back at the dock were just as rewarding. 

Bart found enormous joy in spending time with people, old friends and new alike, especially outdoors. He made friends easily because he was genuinely interested in others. People felt seen, heard, and valued in his presence. He nurtured friendships with care and consistency, making time for people near and far. Wherever Bart traveled, he seemed destined to run into someone he knew, even in Tonga on his honeymoon. 

His deep kindness, generosity of spirit, total absence of judgment, and unwavering faith in people reflected a profound love of life. He met every challenge with grace, humor, optimism, and, always, with that unmistakable twinkle in his eyes. 

A celebration of Bart’s life will be held on Monday, August 3 at 11:00 am at Trinitarian Congregational Church in Concord, Massachusetts, followed by a reception at the Concord Country Club.  To view the service remotely, please click here to access the church live stream.  

Arrangements have been entrusted to Dee Funeral Home & Cremation Service of Concord.