Park on East Main Street on a Friday evening and you'll see the same thing you see most weekends: a line forming outside Southern Roots before the doors open at 11, a table of regulars at SidWill's Cafe & Catering finishing lunch past the usual hour, someone crossing the street from Kapadokia Grill to Simply Thai because they couldn't decide. Six or seven storefronts, all walkable, all doing steady business on a two-block stretch of downtown.
What most people treating Jamestown as a dinner stop don't realize is that the same street keeps going. Main Street doesn't stop at the restaurant row. It runs west, past the shops, and ends at the gate of High Point City Lake Park, a 540-acre lake with its own trailhead into a paved greenway system that stretches toward Greensboro. The dinner and the lake day aren't two separate plans. They're the same street.
The park at the end of your street is also a trailhead
City Lake Park sits at 602 W. Main St., despite carrying High Point's name in its title. The 24-acre developed core of the park, the carousel, the train, the aquatic center, sits on the shore of a lake more than twenty times that size, and the paved Bicentennial Greenway begins right there at the Piedmont Environmental Center on the lake's edge. That's the detail most casual visitors miss: the park isn't a cul-de-sac. It's an entrance.
From the Piedmont Environmental Center trailhead, the greenway runs north along the lake shore, passes the Jamestown Park golf course, and crosses East Fork Road before continuing on toward Gibson Park. The mileage breaks down like this, according to the city's own trail documentation:
| Segment | Distance |
|---|---|
| Piedmont Environmental Center to E. Fork Road | 1.1 miles |
| E. Fork Road to Gibson Park | 2.2 miles |
| Bicentennial Greenway and Deep River Trail Loop (paved greenway into dirt singletrack) | 3.3 miles, about 1 to 1.5 hours |
| Deep River Loop via Bicentennial Greenway at Penny Road | 5.6 miles, about 2 to 2.5 hours |
Somebody who walks off a Southern Roots dinner assuming they're just stretching their legs around the lake has the option, if they keep going, of a 3.3-mile loop that mixes pavement and forest trail, or a longer 5.6-mile version that follows the Deep River corridor before circling back. Neither requires a car. Neither requires leaving the street the restaurants are on.
What's actually open on that stretch of Main Street right now
The food row isn't hypothetical. As of this summer, the working list on and around East and West Main includes Southern Roots at 119 E Main St for Southern plates, Full Moon Oyster Bar a few doors down at 103 West Main Street for seafood, Kapadokia Grill for Mediterranean and Turkish food, Peppers for Indian, Simply Thai directly across the street from one of its neighbors, Black Powder Smokehouse for barbecue, SidWill's Cafe & Catering for a slower breakfast or lunch, and Earl's Landing as another sit-down option on the same corridor.
That's a genuine range for a downtown this size, and it's dense enough that picking a place isn't really the decision. The decision is whether you eat first and walk after, or walk first and eat as the reward.
The lake itself, and why the pool schedule is about to change
The lake and its trails are open on a longer, steadier schedule than most visitors expect. Grounds hours run 7 a.m. to 8 p.m. through September 6, then shift to 7 a.m. to 7 p.m. from September 7 through October 4, according to the City of High Point's park page. That covers the marina, the train, the carousel, and access to the greenway.
The aquatic center runs on a narrower calendar. Daily pool operation ran from June 1 through August 9. As of today, August 15, the pool has shifted to weekends-only, a schedule that holds through Labor Day, September 7. If your plan involves the splash pad or the lazy river specifically, this is the window where you need a Saturday or Sunday, not a Tuesday.
That pool is worth mentioning because it's new enough that longtime residents remember when it wasn't there. The original pool, built in the 1930s and once one of the largest in the Southeast, closed in 2019 and stayed closed for nearly four years while the city carried out a renovation funded by a bond referendum of close to $10 million. It reopened over Memorial Day weekend in 2023 with a 50-meter competition pool, a separate zero-depth leisure pool with a splash pad, three water slides including a side-by-side racing slide, and a renovated locker room building, according to WFMY's coverage of the reopening. The train, carousel, and lake access never stopped operating during that renovation. The trail was always there. The pool is the part that came and went.
The parts of the loop that regulars use and visitors skip
Two features of the greenway don't show up in a quick visit to the park itself. One is Jamestown Park golf course, which the trail runs directly alongside on its way north, giving walkers and runners a stretch of open fairway views without ever setting foot on the course. The other is Gibson Park at 5207 W. Wendover Ave., roughly 3.3 miles up the greenway from the Piedmont Environmental Center, which functions as a second trailhead and a natural turnaround point if you're not going the full distance to the Deep River loop.
The 3.3-mile Bicentennial Greenway and Deep River Trail Loop starts paved and shifts into dirt singletrack, which is the version most people run before work. The 5.6-mile Deep River Loop via Bicentennial Greenway at Penny Road is the one that turns a Saturday morning into an actual outing, closer to two and a half hours if you're not rushing. Both start at the same spot on the lake shore. The difference is just how far you feel like going once you're already there.
Treat it as one afternoon, not two errands
The habit worth building isn't complicated. Eat on Main Street, then walk the length of it to the lake instead of driving somewhere else afterward. Use the greenway as far as you want, whether that's a lap around the water, the 3.3-mile loop through the Deep River singletrack, or the full 5.6-mile version past Gibson Park and back. Check the aquatic center's weekend-only window if the kids want the splash pad, and don't count on it landing on a weekday between now and Labor Day.
Jamestown residents already know pieces of this. What tends to get missed is that it's one continuous stretch of ground, not a restaurant district and a separate city park that happen to share a zip code. If you're new to town and still mapping out the neighborhood, the Jamestown neighborhood guide has more on what else is nearby, and our earlier piece on what it's actually like living in Jamestown covers the day-to-day beyond this one loop.
If you're weighing a move to Jamestown or wondering what a home near this stretch of Main Street is worth, the team at Carolina Home Partners knows this corridor block by block. Reach out any time for a conversation about the neighborhood, no obligation attached.
