How much of Covington's holiday season can you reach without leaving the few blocks between the Southern Hotel and the Covington Trailhead? In 2026 the answer is nearly all of it. The first event is on Thanksgiving Eve and the last is on New Year's Eve, and both take place at the corner of Boston and New Hampshire.
That short stretch has carried the town's December for a while. This year adds a new ending. The Southern Hotel is presenting New Year on New Hampshire, a first-year celebration on Thursday, Dec. 31 that takes over the hotel and the street outside it. So the season now opens and closes at the same address, 428 E. Boston St.
A lot of the season also works as a collection drive for the Northshore Food Bank. You'll see that in the canned goods at the parade, the tree trail on the Trailhead lawn and the canned-goods donations at the tree lighting.
The season on one page
| Date | Event | Where | Cost |
|---|---|---|---|
| Wed., Nov. 25 | Thanksgiving Eve courtyard music, 6 to 9 p.m. | Southern Hotel, 428 E. Boston St. | Free |
| Sun., Nov. 29 | Merry Market | The Greenwood | Varies |
| Dec. 1 to Jan. 6 | 12 Days of Christmas lighted displays, dusk to dawn | Downtown historic district | Free |
| Dec. 1 to 31 | Trim the Trailhead tree trail | Covington Trailhead | Free to view |
| Wed., Dec. 2 | Holiday Sip and Shop | Southern Hotel | Varies |
| Sat., Dec. 12 | Lollipops Christmas Parade, 3 p.m. | Jefferson to Columbia to Boston to New Hampshire | Free, canned goods welcome |
| Sat., Dec. 12 | Christmas in Covington and tree lighting, from 4 p.m. | Covington Trailhead, 419 N. New Hampshire St. | Free, canned goods encouraged |
| Sun., Dec. 13 | History & Holly Home Tour, 2 to 5 p.m. | Historic Covington | $28.29 with fees |
| Fri., Dec. 18 | Covington by Candlelight, 6 to 7:30 p.m. | Covington Trailhead | Free |
| Thu., Dec. 31 | New Year on New Hampshire | Southern Hotel and New Hampshire Street | Varies |
The corner that opens it
Christmas at the Southern runs daily from Nov. 25 through Jan. 1, 2027. It opens the night before Thanksgiving with free live music in the courtyard from 6 to 9 p.m., with food and drinks for sale. For the rest of the season the hotel is decorated inside and across the grounds. The Cypress Bar serves specialty cocktails, and on Fridays there's live piano in the lobby from 5 to 7 p.m.
Two shopping dates come next. The Merry Market at The Greenwood is on Sunday, Nov. 29, and the hotel hosts a Holiday Sip and Shop on Dec. 2. The Gloriette, the hotel's restaurant, is serving on Christmas Eve and Christmas Day. Families can book Santa photos at the hotel through Eventbrite. A session is listed at $48.64 and includes one digital download.
The hotel's December program ends with New Year on New Hampshire, so the place that hosts the first night of the season also hosts the last.
The parade turns onto New Hampshire by the hotel
On Saturday, Dec. 12, the Lollipops Marching Group holds its 5th annual Christmas parade at 3 p.m. It brings Santa downtown, and his ride ends where New Hampshire Street meets the Trailhead. The published route runs like this:
- Start at the corner of N. Jefferson Ave. and W. 27th Ave.
- Travel along Jefferson to Columbia Street, then turn right.
- Turn right again onto Boston Street.
- Turn right onto New Hampshire next to the Southern Hotel.
- Drop Santa at the Covington Trailhead, 419 N. New Hampshire St.
- End at N. Theard and E. 24th Ave.
Dance teams, cheerleading and marching groups and ROTC units march in it, and the parade supports the Northshore Food Bank. The organizers ask spectators to bring canned or non-perishable goods. The Lollipops describe themselves as a sisterhood of women who dance and serve the community. The Christmas parade is how they support the food bank.
Once Santa arrives, the City of Covington's 5th annual Christmas in Covington begins at the Trailhead at 4 p.m. It has kids' crafts, entertainment and the lighting of the Christmas tree. Admission is free, and the city asks attendees at both the parade and the tree lighting to bring canned goods for the Northshore Food Bank.
The Trailhead lawn as a tree trail
Before the parade arrives, the Trailhead lawn will already have been filling with trees for most of December. Trim the Trailhead runs Dec. 1 through 31. The Northshore Food Bank invites businesses, families, organizations and community groups to decorate trees for display there, to raise awareness of food insecurity.
A tree sponsorship costs $500. It covers a 6- to 7-foot live tree, a stand, solar lights and a sponsor sign. Each sponsor is also listed on the city's 12 Days of Christmas map and event webpage. The food bank names Paradiem as its 2026 Christmas Tree Trail Sponsor.
That listing on the city map ties the tree trail to the city's lights. The free 12 Days of Christmas displays put 12 lighted silhouettes at spots around the downtown historic district. They're lit from dusk to dawn every night from Dec. 1 through Jan. 6, 2027, and the Covington Trailhead is stop No. 8. If you walk the silhouettes after dark, the tree trail is one of the stops.
The Trailhead hosts one more evening before Christmas. Covington by Candlelight is on Friday, Dec. 18, from 6 to 7:30 p.m., with a sing-along and performances. Admission is free.
The afternoon the houses open
Most of the season happens outdoors or in the hotel. For one Sunday it moves inside private homes. The Covington Heritage Foundation's History & Holly Home Tour is on Dec. 13 from 2 to 5 p.m. It takes guests through historic Covington and into decorated homes, and the proceeds support the foundation's preservation work. Tickets are $28.29 including fees on BonTempsTix, and pickup instructions will be emailed before the event.
This is the tour's second December in a row. The foundation also held History & Holly on Dec. 14, 2025. The Southern Hotel takes the season's first and last nights. The home tour lands in the middle of December, on the Sunday after the parade.
Dec. 31 brings the season back to the corner
New Year on New Hampshire is new for 2026, and it gives Covington's holiday season a closing night downtown. The Southern Hotel describes a night of music and dining across the hotel and New Hampshire Street, with special menus at participating restaurants. The Cypress Bar and The Gloriette are named as part of the evening. The hotel is posting updates on its Facebook page as the date gets closer.
The same few blocks also hold a newer restaurant. Where Y'at reported that The Hampshire launched at 401 N. New Hampshire St. at the tail end of summer, with Chef Ryan Gall leading the kitchen. Gall co-owns The Hampshire with General Manager Jonathan Cimino. The address is next to the Trailhead at 419, near the end of the parade route and the edge of the tree trail.
One stretch of a single street gets the Thanksgiving Eve courtyard music, Santa's arrival, a lawn of food bank trees, a candlelight sing-along and now New Year's Eve. If you plan to sponsor a tree, the $500 sponsorship form is on the Northshore Food Bank's site, and the trail opens Dec. 1.
If this December has you thinking about life within walking distance of New Hampshire Street, or about what a historic Covington home looks like up close, Allison Vencil knows these blocks and is happy to talk them through with you. Let's Connect.
