A retaining wall fails from water, not weight. Get the drainage right and the wall lasts decades; skip it and the wall leans in five years.
In Connecticut, the frost line sits about 42 inches down. A footing above it heaves every winter and settles every spring, and the wall rides along. Segmental block walls sit on a compacted gravel footing rather than a poured one, but the depth rule is the same: below frost, compacted, and level.
The zone directly behind the wall should be clean gravel, typically at least 12 inches deep, so water drains down instead of sitting against the wall and freezing. Soil backfill holds water, and held water is hydrostatic pressure plus freeze-thaw expansion — the two forces that push walls over.
A perforated drain pipe at the base of the gravel zone, wrapped in filter fabric and daylighting out the end of the wall or to a storm drain, is what actually removes the water. A pipe that dead-ends behind the wall is decoration. Ask where yours daylights.
Even with a drain pipe, the wall needs exits at the base — weep holes in mortared walls, or the natural gaps in dry-laid and segmental construction — so trapped water can escape visibly. If you never see water leave a wall after heavy rain, it is leaving through the wall instead.
Walls over about 4 feet frequently trigger permits or engineering review in Connecticut towns, and taller walls need geogrid reinforcement tying the wall into the backfill. A quote for a 6-foot wall with no mention of permits, engineering, or geogrid is a quote for a wall that will not stay up — or will not stay legal. Build the review time into the schedule, and never let a wall's height be "rounded down" on paper.
Two minutes. Matched with a local masonry contractor. Free written estimate, no obligation.