When to start holiday party outreach, and how far ahead people book

Restaurants, hotels and venues should start their holiday party outreach in July. The companies that want the best December nights usually book them between July and September, and the biggest groups book first. So email your past clients and past inquiries in July. Keep the campaign going through September. Then send the same people a last reminder in mid-October with an offer for the dates still open. If your venue waits until November, you’re left selling the dates nobody else took, or pushing the party into January or February. The venues that run it like pros start even earlier, warming up their contacts in April or May.

That’s the calendar we run at Dexter for venues on Dexter Outreach. Dexter is event sales software for restaurants, hotels and venues to grow event revenue.

When to start, who to email and how often to follow up

• Prime December nights, Wednesday to Friday in the first 3 weeks, usually go to companies that book between July and September. Companies that come back every year often book as early as May, depending on their fiscal year.
• Venues should email two lists first: everyone who booked any event with them, and every inquiry that was never booked or was turned down, from the last 2.5 years. They should exclude anyone they’ve been talking with in the last 6 months, so no live deal gets a campaign email.
• Venues should send two to four follow-up emails to contacts who don’t reply, over the 2 to 3 weeks after the first email. Then everyone gets a last reminder with an offer in mid-October.
• Venues should keep checking whether their emails are landing in spam. Corporate contacts have the heaviest spam filters, so they get fewer emails a day from each sending address.

How far ahead companies book holiday parties

The prime nights in December are Wednesdays, Thursdays and Fridays in the first 3 weeks, and they go first. By the end of October, they’re usually gone. Earlier-week dates and the second half of December fill later, in November and December. More companies are also moving the party into January, especially the middle weeks of the month.

Some companies now plan their parties later. In November 2025, BizBash asked event pros what they were seeing that season. “It does feel like companies have been starting their planning later this year,” said Matt Davis, director of sales and catering for Grill on 21 and The LaSalle Chicago. He added that a later Thanksgiving could be part of the reason (BizBash, Top 4 Corporate Holiday Party Trends of 2025).

Budgets are part of it too. Ashley Okamura, director of events at Hyatt Regency Salt Lake City, told BizBash: “Planning timelines are also shorter than in previous years, which we believe is largely due to those budget constraints.”

The parties still happen. In a Challenger, Gray & Christmas survey of HR and business leaders in late 2024, 64% of companies were planning a holiday celebration, and 17% planned to cut what they spend on it (Challenger, Gray & Christmas, December 10, 2024).

The season, month by month

Build 2 lists first

Your venue’s first holiday emails go to two lists. Closed won is everyone who’s booked any kind of event with you, holiday party or not, and closed lost is everyone who inquired and never booked or was turned down.

Go back 2.5 years for both. Then, to keep a live deal from getting a campaign email, exclude anyone you’ve been in conversation with in the last 6 months.

Split both lists by lead type: corporate, wedding and social. The holiday campaign goes to corporate and social contacts. People who book social events often work at companies that throw holiday parties, and corporate clients have social events of their own.

Many venues aren’t tapping into their past clients and past inquiries, even though those people bring both repeat bookings and new ones. These people already know you, so each email does more than sell December. It reminds them:

• that you exist
• to book
• to think about booking in the future
• to book a regular reservation
• to give you feedback
• about your other locations and offerings, like catering

Write a short first email

A venue’s first holiday email should be short. It should come from the events lead, by name. Build it from these parts:

• Something specific: the event they held with you, or the one they asked about.
• A thank-you with a gift attached, like a round of cocktails, appetizers or dinner, that asks for nothing in return.
• An offer tied to a date, like a dessert bar for the group if they book by the end of August.
• A short call to action: one question they can answer in a line.
• A P.S. about something else you offer, like catering or a sister venue nearby.

Here’s one in that shape, for a corporate client that held a team dinner with you in the spring. The names are examples.

Hi Priya,

We loved having your team in for dinner in April, so I wanted to say thank you. Next time you’re in, the first round of drinks is on me.

We’re also running a holiday party special until August 20th. Book an event by then, and we’ll add a dessert bar for your group.

Have anything coming up?

Talk soon,

Dana

P.S. We cater offsite too, if the office is easier.

For an inquiry that was never booked, the specific line is what they asked about, like a team dinner for 30 in March.

Leave links and imagery out of outreach emails, because in our experience they’re the #1 cause of landing in spam. Save them for the newsletter.

Follow up 2 to 4 times

Follow-ups are where you win a lot of your business. If there’s no reply, send corporate contacts three to four follow-up emails and social contacts two to three, spread over the 2 to 3 weeks after the first email. Corporate contacts are used to follow-ups, while social events are more personal, so go lighter there. Keep each one short and give the reader something new. The shapes that work:

• First, a light bump: offer to send details on your spaces and pricing.
• Next, social proof: a similar event you hosted recently, with an offer to share a sample proposal.
• Last, a soft close: ask whether they’d rather you check back next quarter.

Every “maybe later” is your gold. Note when they want to hear back, and set a reminder in your event management system or inbox so the follow-up actually happens.

Make sure the emails land in the inbox

Deliverability is the piece people forget. An email in the spam folder books nothing, however good the timing and the offer.

Have you ever sent a message through your event management system that showed it was opened 10 times, then called the lead and heard they never got it? That’s a delivery failure. The email never made it past the spam filter, so the open count meant nothing.

An inbox that sends many emails can get flagged as spam over time. So spread your sending across about eight addresses on your venue’s domain, and send 10 to 20 emails a day from each one. Corporate contacts have the heaviest spam filters, so send them fewer a day from each address. Set the addresses up a few weeks before the July send, because new addresses need 2 to 3 weeks to warm up.

Then check where your messages land while the campaign runs. A spam check shows whether they reach the inbox or the spam folder. We use EmailGuard for this. For venues on Dexter Outreach, we monitor deliverability with spam checks.

Get your inquiry form ready for holiday leads

A venue should have their inquiry form ready before the first holiday email goes out. Some people will respond to your holiday outreach through the form instead of replying directly to the email. The season’s new inquiries land in the form too. It should ask what your team needs to sort a holiday lead at a glance:

• A holiday party option under occasion, so those inquiries can be answered first.
• A date and a backup date, because the first choice is often gone.
• The guest count and a budget range, so your team can see which space and menu fit.
• The preferred space, with photos and what each room offers, and your minimums if you choose to display them.
• Your sister venues nearby, selectable in the same inquiry, if you run locations close to one another.

The form should also show your holiday offerings, photos and upsells.

Hotel Chelsea’s events team was fielding 200+ inquiries a week when they upgraded their event form with Dexter Intake. The new form captures budget, date flexibility and space preferences upfront. The team surpassed their revenue goals, and conversion went from 10% to 22% (Hotel Chelsea case study).

Sister venues matter a lot in December, when a company’s first choice is already full. Last season, October 2025 to April 2026, 27% of Golden Age Hospitality’s inquiries arrived in Tripleseat with 2 or more of their New York venues selected. Comparing October to April with the same months a year earlier, their event revenue grew from $1.4m to $2.4m with Dexter (Golden Age Hospitality case study).

Starting in October? Send your final reminders

A venue starting in October should send their final reminders to past clients and past inquiries in mid-October. Keep them going until early November. Lead with a special offer for the dates you know won’t book on their own, like weekday lunches and earlier-week dates.

Add a January deal for companies whose December date is gone, and send the reminder from your events lead.

Late dates still book. “One positive is that many seem to be celebrating throughout all of December and into January, leading to additional availability for us to cater to more groups,” Matt Davis told BizBash. Offer those dates by name to everyone who asked for a night that was already taken.

Measure each list while the campaign runs

Response rate is the number to watch first.

• Response rate: genuine replies divided by the contacts the email reached. In our experience at Dexter, a good response rate on a warm list of about 1,000 contacts is 6 to 9%.
• Interest: how many replies are interested, and how many say maybe later.
• Bookings and revenue from each list, including the people who booked without replying.
• Bounces and contacts who’ve left the company, so the list is clean before the October reminders.

Then judge the campaign on the revenue it booked, against what it cost.

How Dexter does it

Dexter’s Outreach runs the holiday campaign, and Intake takes the inquiries it brings in. Insights tracks the bookings and revenue that follow.

A venue on Tripleseat can re-engage past leads from Tripleseat itself. For venues that don’t have the hours, Dexter Outreach runs the whole campaign at scale, follow-ups included. It re-engages the past event leads already in Tripleseat or the venue’s inbox, sorted into the same two lists, and sets up and warms up the sending addresses. It writes the emails in the venue’s voice and sends them from a named member of the venue’s events team, and replies go straight to that person. The same lists carry the July campaign, the follow-ups and the mid-October reminder. You can see two of these campaigns with their live results: New Realm Brewing and Southern Proper Hospitality.

Dexter Intake replaces the generic contact form on a venue’s site, or runs on a branded page the venue links to. It asks what the events team needs to know, shows the venue’s spaces and offerings, and promotes their sister venues nearby while the guest inquires. Each lead goes into Tripleseat, Perfect Venue, another event management system or directly to the venue’s inbox. The guest gets a receipt that repeats back what they submitted.

Dexter Insights comes included. It tracks the venue’s pipeline from inquiry to closed business, including time to first response, conversion rate, cross-sell rate, ghost rate and revenue, with a consultation on what to change.

FAQ

Related reading

• How to re-engage past event leads
• How fast should a venue respond to a private event inquiry?
• I already have a form on my website. Why do I need Dexter?
• What is event sales software, and which venues need it?
• Dexter customer stories

Sources

• BizBash, “Top 4 Corporate Holiday Party Trends of 2025,” Michele Laufik, November 12, 2025. Quotes from Matt Davis and Ashley Okamura are verbatim. bizbash.com
• Challenger, Gray & Christmas, 2024 holiday party survey, December 10, 2024: an online survey of 173 HR and business leaders in November and December 2024. challengergray.com
• Hotel Chelsea and Golden Age Hospitality case studies on teamdexter.com, read October 8, 2026. Every quote is verbatim from those pages, and every figure is as those pages report it.
• Outreach dashboards for New Realm Brewing and Southern Proper Hospitality, insights.teamdexter.com, read October 8, 2026.