Old Saybrook Walking Food Tour by CT Shore Walking Food Tours
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels with basic walking ability; no specialized conditioning needed.
Overview
Take a 3-hour stroll through Old Saybrook’s Magic Mile, combining local bites with fascinating historical stories. CT Shore Walking Food Tours delivers a unique small-group taste of Connecticut’s coastal charm.
Old Saybrook Walking Food Tour
Up to 3 Hours • Ages 12+ • Get to Know the Flavors of Old Saybrook!
Select participants and date
About This Adventure
Experience the Flavor and History of Connecticut's Coastal Towns!
Duration
Up to 3 Hours
About
Diane is looking forward to taking you on a tour of downtown Old Saybrook. As we wander from restaurant to restaurant, she will share some of Old Saybrook's history and information about the area. The tour will be approximately three hours in length. We will meet at a designated spot and walk to three or four restaurants. All restaurants are on the Magic Mile of Main Street in Old Saybrook. Each walk should be no longer than 1.5 miles.
At each restaurant, you will have a carefully prepared small plate. As we wander from restaurant to restaurant, Diane will share some history of Old Saybrook, and information about the area. (Did you know that the first black female pharmacist in Connecticut had her shoppe on Main Street? That General Lafayette stayed in Old Saybrook?) You will experience the food and vibrant retail scene of downtown. At each restaurant, water will be available and other beverages are available for purchase.
Tours are limited to a maximum of eight people. Private tours and specially designed tours are also available upon request.
Adventure Tips
Wear comfortable walking shoes
The route covers about 1.5 miles on mostly paved surfaces, so sturdy, supportive footwear is recommended.
Arrive hungry but ready to pace
Light to moderate appetite works best since portions are small plates paired with leisurely walking.
Hydrate along the way
Water is provided at each stop, but bring a refillable bottle especially for warmer months.
Consider weather-appropriate clothing
Tours run year-round; dress in layers for spring and fall or sun protection in summer.
Local Insights
Wildlife
- Seasonal songbirds common in downtown trees
- Occasional harbor seals visible along the nearby shoreline
History
Old Saybrook was one of the first English settlements in Connecticut, dating back to the early 1600s, with notable events such as General Lafayette’s stay during the Revolutionary War.
Conservation
Local businesses emphasize sustainability by sourcing seasonal ingredients and reducing waste, reflecting Old Saybrook’s commitment to preserving its coastal environment.
Select participants and date
Adventure Hotspots in New Haven, CT
Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
Supports your feet throughout 1.5 miles on paved Main Street.
Water bottle
Helps stay hydrated during warmer months despite water being available at stops.
summer specific
Light jacket or layers
Protects against variable weather and cooler temperatures on the route.
spring|fall|winter specific
Sun protection
Something like a hat or sunscreen shields against sun exposure on open stretches.
summer specific